Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
29.6.1.2.3.1 Variation 1: From Alcohols without Removal of Water

DOI: 10.1055/sos-SD-029-00368

von Angerer, S.; Warriner, S. L.Science of Synthesis, (200729323.

The direct formation of acetals from aldehydes or ketones in the presence of a catalyst strongly depends on the reactivity of the carbonyl group and the nature of the hydroxy component. The reactivity of carbonyl compounds can empirically be ranked in the following order: formaldehyde > aliphatic aldehydes > α,β-unsaturated aldehydes > acyclic ketones, cyclohexanone > cyclopentanone > α,β-unsaturated ketones, α,α-disubstituted ketones >> aromatic ketones.

Mee eeeeee eeeeeeeeeeeee ee eeeeeeeee eeeee eeee eeeeeeeee ee eeeeee eeeeeeee, eeeeeee eee eeeeeeeeee ee eeeeeee eeee eeeeeee eee ee eeee eeeeeeeee, eeeeee ee eee eeee ee eeeeee eeeeeee, eeeee eeeee eeeee eeee.[‌888‌] Mee eeeeeeeeee ee eeeeeeee eeeeeeeee eeee eeeeeee ee eeeeeeee eeeeeeee eeeee ee eeeeee eeeeeee. Meeeeee eee eeeeeee eeeeeeeeeeeee eee eeeeee eeeeeeeeeeeee eeeeeeeee. M eeeee eeeeee ee eeeeee eeeeeeeee eeee eeee eeee eee eee eeeeeeeeeee ee eeeeeee 88, eeeeeeeee eeeeeeeee[‌888‌‌888‌] eee eeeeee eeeeeee eeeee,[‌888‌‌888‌] eeeeeeee eeeee,[‌888‌,‌888‌] eee-eeeeeeee eeeeee,[‌888‌,‌888‌] eee Meeee eeeee eeee ee eeeeee(eeeeee)eeeeeee[‌888‌,‌888‌] eee eeeee eeeeeeeeeee[‌888‌] (Meeee 8). Mee eeeeeeeeeeee Meøeeeee eeee eeeeeeee-8,8-eeeeeeeeeeee eeee eee eeee eeeeeeeeeeee eeee ee eee eeeeeeeeeee ee eeeeeee eeeee eeee eeeeeeeeee.[‌888‌] M eeeeeee ee eeeee eeeee, eeeeee eeeeeeeee,[‌888‌‌888‌] eeee eeee eeee eeee ee eeeeeeeee. M eeee eeeeeeeee eeeeeeeee eeeeee eeeeeeeee e eeeeeeeee eeeeee ee eeeeeeee(MMM) eeeeeeee eee eeeeeeeee eeee ee eeeeeeee.[‌888‌] Meeeeee(MMM) eeeeeee eee eeee eeeee ee eee eeeeee ee eeeeeeeeeee eeeeeeeee eee eeeeee eeeeeeeeeeeee.[‌888‌] Meee ee eeeee eeeeeeeee eeeeeeeee e eeeeeeeeeeeeee eeeeeeeee ee eeeeeeee eeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeee.[‌888‌‌888‌] Meeeeeeee eee eeee eeeeeee eee eeeeeeeee eeee eeeee eeeeeeee eeeeeee ee eeee eeeee eeee eeeeeeeeee ee eeeeeeee eeeeeeeeee 8.88 eeeeeeeeeee ee eeeeeeeee eee eeee ee eeeeeeee eeeeeeee.[‌888‌] Meeeeeeee eeeeee eee eeee eeee eeeeeeeeee ee ee eeeeeeeee eeeeeeee eee eee eeeeeeeeee ee eeeeeeeee eee eeeeeee eeee eeeeeee.[‌888‌] Mee eeeeeeee eeeeeeee eeeee eeee eeeeeeeeee ee eee eeeeeee ee eeee eee eee eeeeee eee eeeeeeeee. Meee eeeeee eeee eeeeee eee eeeeeeeee eeeeeeeeeeeee ee eeeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeee.[‌888‌]

Meeee 8 Meeeeeeee ee Meeeeee ee Meeeeeee ee Meeeeeeee ee Meeeeee eeee Meeeeeee eeeee Meeeee Meeeeeeeee eeeeeee Meeeeee ee Meeee[‌888‌,‌888‌‌888‌,‌888‌,‌888‌,‌888‌,‌888‌‌888‌,‌888‌‌888‌]

M8 M8 M8 Meeeeeee Meeeeeeeee Meeee (%) Mee
8-MeM8M8 M Me 8M MMe MeMM, ee, 88eee 88 [‌888‌]
(MM8)8MMe(MM8)8 Me MMe (eeeeee) MeMM, eeeeee, 88e 88 [‌888‌]
8-MeMM8M8 M Me M8MM8 MeMM, 88°M 88 [‌888‌]
(MM8)88Me M Me 8-eeeeeee-8-eeeeeeeeeeee eeee eeeeee, eeeeee, 8e 88 [‌888‌]
8,8-Me8M8M8 M Me eeeeeeee-8,8-eeeeeeeeeeee eeee ee, 88e 88 [‌888‌]
Me M MM8MM=MMMe MeMe8, MMe ee, 8e 88 [‌888‌]
Me M MM8MMM MeMe8 ee, 8e 88 [‌888‌]
8-M8MM8M8 M Me MeMe8 (eeeeeee eeeeeeeee) eeeeeee, 88°M, 88e 88 [‌888‌]
MM=MMMe M Me MeMe8 MeMM, eeeeee, 8.8e 88 [‌888‌]
eMe M Me MeMe88M8M MeMM, ee, 88e 88 [‌888‌]
8-MeMM8M8 M Me eeeee MeMe8 MeMM, ee, 8e 88 [‌888‌]
(MM8)8MM(e-Me)(MM8)8 Me Me8+-eeeeeeeeeeeeeee MeMM, ee, 88eee 88 [‌888‌]
(MM8)8 Me Me8+-eeeeeeeeeeeeeee MeMM, ee, 88eee 88 [‌888‌]
(MM8)8Me Me Me MeMe8, Me MeMM, ee, 88e 88 [‌888‌]
8-MeM8M8 M Me Me(MM)8 MeMM, ee, 8e 88 [‌888‌]
Me M Me eeeeeeeee MeMM, eν, 88eee 88 [‌888‌]
8-M8MM8M8 M Me M8 MeMM, ee, 8e 88 [‌888‌]

Meeeeeeeeeeee eeeeeeeee ee eeeeeeee eeeeeee eee eeee eeeeeeee eee eeee 8-eee-8β-eeeeeeee eeeee eeeee eeee eeee eeee eeeeeeeee ee eeeeeeee (Meeeee 88).[‌888‌] Meeeeee eeeeeee ee eeeeeeeeeee eeeeee eeeeeeeee eeeeee eeeeee eee eeeeeeeee-eeeeeeeee eeeeeeeeeeeee ee e α,β-eeeeeeeeeee eeeeee eeeeeee ee eeeeeeee, eeeee eeeee eee eeeeeeeee eeeeeee ee eeeeeeee eeeee.[‌888‌]

Meeeee 88 Meeeeeeeeee Meeeeeeeeeeee ee eee 8-Mee Meeeeeee ee Meeeeeee Meeee[‌888‌]

Mee eeeeeeeeeeeee ee eeeeeeeeeee eeeeeeeee eee ee eeeeeeeeeee ee eeee eeeeeeeee. Meee 8-eeeeeeeeeeeeeee-8-eee-8-eeeeeeeeeeee eeeeee eeee eeeeeeee ee eee eeeeeeee ee eeeeeeee eeeeeeee, eee eeee eeeee ee eeeeeeeeee ee eeee 8-(eeeeeeeeeeeeeee)eeeeeeeeee-8-eee ee eeee eeeee.[‌888‌] Meee α,β-eeeeeeeeeee eeeeeeeee eee eeeeeee eeee ee eeeeeee ee eee eeeeeeee ee eeee, eeee eeeeeeeeeeeee eee eeeeeeee ee eee eeeeeee eeeeee eee M=M eeee eeeeee. Me eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeeeee eeeeeeee, eee-8-eeee ee eeeeeee eeeeeeeee eeee 8,8,8-eeeeeeeeeeeeeeee (Meeeee 88).[‌888‌,‌888‌] Meee eeeeeee, eeeeeeeee eeee eeeeeeee eeeeeeee, ee eeee ee eee eeeeeeeee eeeeeeeee, 8-eeeeee-8,8-eeeeeeeeeeeeee ee eeeeeeee ee eeeeeeeeee eeeee.[‌888‌]

Meeeee 88 Meeeeeeeee ee Mee-8-eeee eeee 8,8,8-Meeeeeeeeeeeeeee[‌888‌]

Meeee eeee eeeeeeeee, eeeeeeee eeee eeee eeeeeeee eeeeee eee M=M eeee, ee eeee 8,8,8-eeeeeeeeeeeeeeee eeee eeeeeee eeee eeeeeee.[‌888‌,‌888‌] Meee eeee eeeeeeee eee ee eeeeeee eeee eeeee eeeeee eeeeeeeeeeeeeeeeee ee eeee ee eee eeeeeeee.[‌888‌]

Meeeeeeee, eee eeeeeeeeeee ee eeeeeee eeee eeeeeeeee ee eeeeeee eeee eeeeeeee ee eeeeeeeee eeeee eeeeee eeeeeeeeee ee eeee Meeee eeeee. Mee eeeeeeeee eeeeeee, ee ee eeeeeeeee eeeeeeeee ee eeee eeeee eeeee eeeeeeeeee. Meee eee ee eeeeeeee eeee eeeeeeee(MM) eeeeeeee ee eee eeeeeeee eee eeeeeee ee eeeeeeeeeeeee ee eee eeee (Meeeee 88).[‌888‌,‌888‌] M eeeee eeeeee ee eeeeeeee, eeeeeeeee, eee eeeeeeeeeee eeeeeeeee eee eeeeee eeeeeee eeee eeee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee eeeeeee 88 ee eeee ee eeeeeeeee eeeeee.

Meeeee 88 Meeeeeeeee ee Meeeeeeee eee Meeeeee eeee Meeeeee eeeee Meeee Meeeeeeeee eeee Meeeeeee(MM) Meeeeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 M8 Meeeee Meeee (%) Mee
8-MeMM8M8 M M 88 [‌888‌]
8-MM8MM8M8 M M 88 [‌888‌]
MM=MMMe M M 88 [‌888‌]
Me M M 88 [‌888‌]
e-Me M M 88 [‌888‌]
(MM8)8 M 88 [‌888‌]
(MM8)8M(MM8)8 M 88 [‌888‌]
(MM8)8 M 88 [‌888‌]

Meeeeee eeeeeeeee eeee eeeee eeeee eeeee eeeeeeeeee eeee (eeeeeeeeeeeee)eeeeeee ee eee eeeeeee eee eeeeeeeee eeeeeeeee ee eee eeee. Meee eee eeeeeeee ee eeeeeeeee ee eeeeeeee, eeeeee eee eeeeeee eeeeeee eee eeeeeeeee eeee eeeeeeee eeeeeee eeee eeeeeeeeeeee eeeeeeeeeeee ee e eeeeeee eeeee ee eee α-eeeeeeee.[‌888‌‌888‌]

Meee eeeeeee eeeeeeeee eee eeee eeeeee ee eeeeeeeee eee eee eeeeeeeeee ee eeeeeeee eeeeeeeee eeee eeeeeee eeeee eeee eeeeeeeeee.[‌888‌,‌888‌] 8-Mee eeeeeeee eee eeeeeeeeeee eeeeeeeee eeee eee eeeeeeeeeeeee 8,8-eeeeeeeee eeeeeeeeeee eeee eeeeeee eeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeee(M) ee eeee eeeeeeeeeee.[‌888‌] Meeeeeeeeee eeeeeeee eee eeeee eeeeeeeeeeee, eee eeee eeeeeeeeee. Meeeeeeeee eeeeeeee eeeeeeee eeeeee eeeeee ee eeeeeeeeee ee eeee eee. Meeeeeeeeeeee ee α,β-eeeeeeeeeee eeeeeeeee ee eeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeee(M) eeeee ee eeeeeeee eeeeeeee (Meeeee 88).[‌888‌] Mee eeeeeeeee eeeeeeeee, eee eeeeeeeee eeeeeeeeee ee eeee eeeee.

Meeeee 88 Meeeeeeeeeeee ee Mee-8-eeee ee eee Meeeeeee ee e Meeeeee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeee Meeeeee 88; Meeeeee Meeeeeeee Meeee Meeeee(MM) Meeeeeee:[‌888‌]

M eeeeeee ee eee eeeeeeee (8eeee), MeMe8 (8eee%) (eeeee ee 888°M eee 8e eeeee ee eee), eee eeeee eeeeeee (8eM) eee eeeeeeee eee 8.88.8e eeeee e MeMe8 eeeee eeee. Meeee eee eeeeeeee eeeeeeee eee eeeeeeee (ee eeeeeeeee ee MMM), eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee e eeeeeee, eeeee eee eeeeeee eeee MeMMe (8eM). Mee eeeeee(MM) eeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeee (eeeee eeeeeeeeeeeee ee 8.8eM eeeee eeeeeee eeeeeeee) eeeeeee e eeeee eeeeee (eeeee eeeeeee, MeMMe/eeeeee 8:88) ee eeeeeee eee eeeeeeeeeeee eeee eeeeee; eeeee: 8888%. Mee eeeeeeeee eeeeee(MM) eeee eeeee ee eeeeee eeeee eeeeee.

Meeeeeee Meeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeee(MMM) Meeeeeee:[‌888‌]

M eeee ee eee eeeeeeee (88eeee), eee eeeeeee (8eM), eee MeMe88M8M (8.88eeee) eee eeeeeee ee ee eee 88e. Mee eeeeeee eee eeeeeee eeee M8M eee eeeeeeeee eeee MM8Me8 (8 × 88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeeee ee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeee 8:88); eeeee: 8888%.

Meeeeeee Meeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeee(MMM) Meeeeee:[‌888‌]

Mee eeeeeeee eeeeeeee (8.8eeee) eee eeeeeeeee ee MeMM (8eM) eee Me(MM8)8 (8.8eeee) eee eeeee eeeee eeeeeeee. Meeee eee eeeeeeee eeeeeeee eee eeeeeeee (ee MMM), eee MeMM eee eeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeeee eeee MM8Me8, eeeeee eeee eee. MeMMM8 eeee, eeeee (Me8MM8), eee eee eeeeeee eee eeeeeeeeee. Mee eeee eeeeeeee eeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeee eeeeeee, MeMMe/eeeeee 8:8); eeeee: 8888%.

Meeeeeee Meeeeee 88; Meeeeee Meeeeeeee Meeee Meeeee:[‌888‌]

Mee eeeeeeee eeeeeeee (8eeee) eee eeeeeeeee ee MeMM (8eM) eee M8 (8.8eeee) eee eeeee, eeee eeeeeeee. Meeee eee eeeeeeee eeeeeeee eee eeeeeeee (ee MMM; 88e eee eeeeeeeee, 8e eee eeeeeee), eee MeMM eee eeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeeee eeee MM8Me8, eee eeeeeeee eeee eeeeee eeee eee. MeMMM8 eeee eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeeeeee. Meeeeeeeeeee eee ee eeeeee eeeeeeeeeeeeee (eeeee eeeeeee, MeMMe/eeeeee 8:8); eeeee: 8888%.

8-Meeeee-8,8-eeeeeeeeeeeeeeeeeee [88, M8,M8=(MM8)8MMe(MM8)8; M8=Me]:[‌888‌]

8-Meeeeeeeeeeeeee-8-eee (888e, 8eee), MeMM (8.8M), eee e 8.8M MMe eeee ee eMeMM (888eM, 8.8eee) eeee eeeeeeee eee 88e. Meeee eeeeeee ee ee, eee eeeeeee eee eeeeeeeeeee ee eeeeee Me8MM8 (888e, 8.8eee). Meee, eee eeeeeee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. M eeee ee MeMMM8 (888e, 8eee) ee M8M (8M) eee eeeee ee eee eeeeeee. Meeee eeeeeeee eee 88e, eee eeeeee eee eeeeeeeee eeee eeeeeee (8 × 8M, 8 × 8.8M). Mee eeeeeee eeeeeee eee eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeeee eeeeee; eeeee: 888e (88%); ee ee eee eeeeeeeeeeeee: 888°M.

8,8-Meeeeeeeeeeeeeeeeeee [88, M8,M8=(MM8)8; M8=Me]; Meeeeee Meeeeeeee Meeee ­Meeeee(MMM)-Meeeeeeee Meeeeeeeeeeeeee:[‌888‌]

Me e eeeeeee ee eeeeeeeeeeeee (888ee, 8.88eeee) eee eeeee MeMM (88eM) eee eeeee Me8+-eeeeeeeee eeeeeeeeeeeeeee (88ee, 8.8888eeee ee eeeeee eeee eeeee) ee eee eeeeeee ee 88°M, eeee eeeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee ee ee eee 88eee. Mee eeeeeeee eee eeeeeee ee eeeeeee eeeeeeeeee eee eeeeee eeee MM8Me8 (88eM). Mee eeeeeeee eeee eeeeeee ee eeeeeeeeeeee eeee e Meeeeee eeeeeeeee ee eeeeee eeeeeeee ee eeeee e eeeeeeeee eee; eeeee: 888ee (88%).

Meeeeee 88; Meeeeee Meeeeeeee:[‌888‌,‌888‌]

Meeeee M:[‌888‌] Mee eeeeeee eeeeeeeee eeeeeeee (8eeee) eee eeeeeeeee ee MeMM (88eM). Me eeee eeee-eeeeeee eeee, eeee ee 8°M eeeee M8, eee eeeee eeee e eeeeeee, ee eee eeeeeee, e 8.8M eeee ee MeMe8 ee MM8Me8 (88 µM, 8.88eeee). Meeee ee. 88eee, MM8 eee eee eeeeeee eeee eee eeee ee 8°M. Mee eeeeeeee eee eeeeeee eeee MM8Me eeeeeee ee eeeeeeeeeee ee e eeeee eeeee eeee eee eeee (eM ~88). Mee eeeeeeeeeeeee eeeeeee eee eeeeeee ee ee eee ee eeeeeeeeee 88eee. Meee, M8M (8eM) eee eeeee eee eee eeeee eeee eee eeeeeeeee eeee Me8M (8 × 88eM). Mee eeeeeee eeeeee eeee eeeeeeeee, eeeeee eeee M8M (8 × 8eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Me eee eeeeee ee 8M MMM eee <88%, eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee ee ee Meeeeeeee eeeeeeeeeeee; eeeee: 8888%.

Meeeee M:[‌888‌] Mee eeeeeeeee eee Meeeee M eee eeeeeeee, eeeeee eeee MeMe8 (8.88eeee) eee eeeeeeee; eeeee: 8888%.

Meeeee M:[‌888‌] M 8.8M MeMe8 eeee ee MM8Me8 (8.88eeee) eee eeeee ee eee eeeeeee eeee e eeeeeee ee e eeeeeee eeee ee eee eeeeee eeeeee (8eeee) ee MeMM (88eM) ee ee. Meeee ee. 88eee, Me8M (8.8eeee) eee eeeee ee eee eeeeeeeee eeee, eeeee eee eeeeeee eee ee eeeeeeeeee 88eee eeeeee eee eeeeeeee ee M8M (8eM). Mee eeeeeee eee eeee eeeeeeeee eeee Me8M (8 × 88eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Me eee eeeeee ee 8M MMM eee <88% eee eeeee eeeeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee; eeeee: 8888%.

References