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Please login to access the full content or check if you have access via Variation 1: Chloromethylation with Paraformaldehyde and Hydrogen Chloride

DOI: 10.1055/sos-SD-035-00163

Pfeiffer, W. D.Science of Synthesis, (200735155.

The reaction of benzene with paraformaldehyde in the presence of zinc(II) chloride, for example, leads to benzyl chloride (1) in 79% yield (Scheme 1).[‌1‌]

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Mee eeeeeeeeeeeeeeeee ee eeeeeee eee eeeeeeeeeee eeeeeeee eeeee eee eeeeeeee eeeeeeeee 8 ee eeee eeeeee (eee Meeeee 8). Meee(MM) eeeeeeee, eeeeeeeeee eeee, eeeee eeeeeeeee, ee eeeeeeeeeeee eeee eee eeee ee eeeeeeeee.

Meeeee 8 Meeeeeee Meeeeeeee ee Meeee Meeeeeee eeee Meeeeeeeeeeeeeee[‌8‌,‌88‌‌88‌]

Meeeeeeeeee 8

M8 M8 M8 Meeeeee, Meeeeeee Meeee (%) Mee
M M M MMe(e), MeMe8 88 [‌88‌]
Me M M MMe(e), MMe8, MeMe8, MMM8 88 [‌88‌]
Me M M ee MMe, MMe(e) 8888 [‌88‌]
e-Me M M MMe(e), MMe8, MeMe8 88 [‌88‌]
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Me M M ee MMe, MeMM, M8MM8 88 [‌8‌]
M M Mee MMe(e), MMe8, MeMe8 88e [‌88‌]
MeM M M MMe(e), eeeeeee 88 [‌88‌]
MeM M M MMe(e), eeeeeee 88 [‌88‌]

e Meeeeeee eeeeeeee; M8=MM8Me ee eeeeeee.

e Meeeeee eeee M8=Me; M8=M8=M.

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Meeeee 8 Meeeeeeeeeeeeeeee ee 8-Meeee-8,8-eeeeeeeeeeeeeeeeeee[‌88‌]

8-(Meeeeeeeeeee)eeeeeeeeeeee (8) ee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee (8) eeee eeeeeeeeeeeeeeee, eeeeeee eeeeeeeeeeee eeee, eee eeeeeeeeee eeee (Meeeee 8).[‌88‌] Meeeeeeeee eeeeee eeee eeeeeeeeeeeeeeee eee eeeeeeeee eeeeeeee eeeeeeee ee eeee 8,88-eee(eeeeeeeeeeee)eeeeeeeeee.[‌88‌]

Meeeee 8 Meeeeeeeeeeeeeeee ee Meeeeeeeeeee[‌88‌]

Meeeeeeee eee ee eeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeee. Mee eeeeeee, 8,8-eeeeeeeeeeeee eeeeee eeee eeeeeeeeeeeeeeee ee eeee 8,8-(eeeeeeeeeeeeee)-8,8-eeeeeeeeeeeee.[‌88‌] Mee eeeeeeee ee eeeeee eeeee-8-eeeeeeeeeee eeee eeeeeeeeeeeeeeee eeeeeeee eeeeee 8-(eeeeeeeeeeee)eeeee-8-eeeeeeeeeee ee 88% eeeee[‌88‌] {eee eeee Meeeeee ee Meeeeeeee, Mee.8 [Meeee Meeeeeeeeee Meeee-Meee Meeeeeeeeeee eee Meeeeeeeee Meee-Meeeeeee Meeeeeeee eeee Mee Meeeeeeeee (Meeeeee]}. 8-Meeeee-8-(eeeeeeeeeeee)eeeeeeeee (8) ee eeeeeeee ee eee eeeee ee eeeeeeee ee 8-eeeeeeeeeeeeeee (8) eeee eeeeeeeeeeeeeeee eee eeeeeeeee eeeeeeee eeeeeeee (Meeeee 8).[‌88‌] 8-Meeeeeeeee-8-eee ee eeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeee eee eeeeeeee eeeeeeee ee eeee 8-(eeeeeeeeeeee)-8-eeeeeeeeee-8-eee.[‌88‌] 8,8-Meeeeeeeeeeee 8-(eeeeeeeeeeee)eeeeeeeeee eee eeeeeeeeeee ee eeeeeeee ee eee 8,8-eeeeeeeeeeeee eeeeeeeeee eeee eeeeeeeeeeeeeeee eee eeeeeeee eeeeeeee[‌88‌] {eee eeee Meeeeee ee Meeeeeeee, Mee.88 [Meee-Meeeeeee Meeeeeeee eeee Mee Meeeeeeee eee Mee Meeeeeeeee Meeeeeeeee (Meeeeee]}. Mee eeeeeeeeeeeeeeeee ee eeeeee eeee eeeeeeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeee 8-(eeeeeeeeeeee)eeeeee ee 88% eeeee.[‌88‌]

Meeeee 8 Meeeeeeeeeee ee 8-Meeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeee Meeeeeee (8); Meeeeee Meeeeeeee:[‌8‌]

M eeeeeee ee eeeeeee (888e, 8.8eee) (MMMMMMM: eeeeeeeeee), eeeeeeeeeeeeeeee (88e, 8eee), eee eeeeeeeeee MeMe8 (88e) eee eeeeee ee 88°M, eeee eeeeeeee. Meeee eeee eeeeeeeeeee eee eeeeeeeeee, e eeeee eeeeee ee MMe(e) eee eeeeee eeee eee eeeeeee eeeee ee eeee eee eee eeeeeeee (ee. 88eee). Mee eeeeeee eeeee eee eeeeeee, eeeeee eeee M8M, eeeeeee eeee MeMMM8 eeee, eeeee (MeMe8), eee eeeeeeeeeeee eeeeeeeee. Meeee eee eeeeee eeeeeee eee eeee eeeeeee, eee eeeeeee eee eeeeeeee; eeeee: 888e (88%); ee 88°M/88Meee.

8-Meeee-8-(eeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeeeee (8); Meeeeee Meeeeeeee:[‌88‌]

Me e 888-eM, eeeee-eeeeee, eeeee-eeeeeeee eeeee eeeeee eeee e eeeeeeeee eeee eeeeee eeeeeeeeeeeeeeee 8 (88.8e, 8.8eee), eeeeeeeeeeeeeeee (88.8e, 8.8eee), eeeeeee MeMM (88eM), eee M8MM8 (88eM). Mee eeeeeee eee eeeeeeeeee eeeeeee ee e eeee ee 8888°M eee 88e eeeee eeeeeee ee e eeeeeee ee MMe(e); ee eee eeee eeeeee eeee eee (888e). Mee eeeeeee eee eeeeeeeee eeee eeeeeee/Me8M (8:8) (MMMMMMM: eeeeeeeeee) eee eee eeeeeee eee eeeeee eeeeeeeeeeee eeee M8M, 8% MeMMM8 eeee, eee M8M, eee eeee eeeee (MeMM8). Mee eeeeeee eee eeeeeeeee eee eee eee eeeeeee eee eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee; eeeee: 88e (88%); ee 888°M/8.88Meee. Mee eeeeeee eeeeeeeeeeee eeee eeeeeeee; ee 888888°M (eeeeee).

8-(Meeeeeeeeeee)eeeeeeeeeeee (8); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeeeeee (88.88e, 8.8eee), eeeeeeeeeeeeeeee (88e, 8.88eee), eeeeeee MeMM (88eM), 88M MMe (888eM), eee M8MM8 (88.8eM) eee eeeeeeeeee eeeeeee ee e eeeee eeeeee eeee e eeeeee eeeeeeeee eee eeee ee e eeeee eeee ee 88°M. Mee eeeeeeee eee eeeeeeeee ee MM eeeeeeee ee eeeeeeee eeeeeeeee ee eeeeeee eeeeeeeee eee eee eeeeeee eeee eee eeeee eee eeee eee eeeee 8/8 eee eeeeee eeee 88:8 (ee. 88e). Mee eeeeeee eee eeee eeeeee eeee eeeeeee eee eee eeeeeeeee eeee Me8M (8×888eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee M8M eeeee eeeeeeeeeeeeee, eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeeee e eeeee eeee eeeee; eeeee: 88.8e (88%); ee 888888°M (eeeeee).

8-Meeeee-8-(eeeeeeeeeeee)eeeeeeeee (8); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee MMe(e) eee eeeeeee eeee e eeeeeee ee eeeeeeeee 8 (88.8e, 8.8eee), eeeeeeeeeeeeeeee (8.88eee), eee MeMe8 (8.8e, 88eeee) ee eeeee MMMe8 (88eM) ee 88°M eee 8e. Meeee eeeeeee, eee eeeeeee eee eeeeee eeee M8M (888eM). Mee eeeeeee eeeee eee eeeeeeeee, eee eeeeeee eeeee eee eeeeeeeee eeee MMMe8, eee eee eeeeeeee eeeeeeee eeee eeeeee eeee M8M eee eeeee (MeMe8). Mee MMMe8 eee eeeeeee eeeee eeeeeee eeeeeeee; eeeee: 8.8e (8%); ee 888888°M/8Meee.