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Please login to access the full content or check if you have access via31.5.1.3.2 Method 2: Rearrangement of Alkyl and Benzyl Aryl Ethers
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González-Bello, C.; Castedo, L., Science of Synthesis, (2007) 31, 322.
Alkyl- and benzylphenols can be obtained from alkyl and benzyl aryl ethers by Brønsted or Lewis acid-catalyzed rearrangement. For example, hydrogen fluoride–antimony(V) fluoride in ethyl and propyl aryl ethers 16 rapidly afford 3-alkylated phenols 17 at −60°C (Scheme 5).[18] Under these conditions, unsymmetrical alkyl aryl ethers, such as 18, give both regioisomeric phenols 19 and 20, in a 2:1 ratio.[18]
Meeeee 8 Meeeeeeeeee ee Meeeeee ee Meeeeeeeeeeee ee Meeee Meee Meeeee[88]
Meeeeeeee ee eee eeeeee eeee eeeeee 88 eeee e eeeeeeeee eeeeee ee eeeeeeeeeeeeeee eeee ee 88°M eeeeeee eee eeee-eeeeeeeeeee eeeeeeeeeeeee eeeeeeee 88 (Meeeee 8).[88] Meeeeeeeeeee, ee eee eeeeeee ee eeee, eee eeeee-eeeeeeeeeee eeeeeee 88 eee eeeeeeee eeee eeeeee eeee eeeeee 88 ee eeee eeeeee.[88]
Meeeee 8 Meeeeeeeeee ee Meeeeee ee Meeeeeeeeeeee ee Meeeee Meee Meeeee[88]
Me e eeeeeee eeeeee ee eee eeeeeeee Meeeeee eeeeeeeeeeeee (Meeeeee 88.8.8.8.8), eee eeeeeeeeeeeee eeeeeeeeeeeee ee eeeee eee eeeeee eeee eeeeee eeeeeee eeeeeee eeeeeeee ee eeeee- eee eeee-eeeeeeeeeee eeeeeee eeeeeeee eeee eee eeeeee eeeeee. Meeeeee, eeeeeeeeeee ee eeeeeeeeeeee eeeee eeee eeeee ee e eeeee eeeeee ee eeeeeee eeeeeeeeeeee eeee e eeee eeeeeeeeeee eeeee-eeeeeeeeeee.[88]
Meeeeeeeeeee Meeeeeeee
8-(8-Meeeeee-8-eeeeeeeeeeee)-8-eeeeee-8,8-eeeeeee-8M-eeeee-8-eee (88, M8 = Me); Meeeeee Meeeeeeee:[88]
M eeee ee 8-eeeeee-8-(8-eeeeeeee)-8,8-eeeeeee-8M-eeeee-8-eee (88, M8 = Me; 88 ee, 8.88 eeee) eee e eeeeeeeee eeeeee ee MMM (8 eeee) ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee ee 88°M eeeee ee eeeee eeeeeeeeee eee 88 e. M8M (8 eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8 × 8 eM), eeeee (Me8MM8), eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeeeeeeeee (MeMMe/eeeeee); eeeee: 88 ee (88%); ee 888–888°M.
8-(8-Meeeeee-8-eeeeeeeeeee)-8-eeeeee-8,8-eeeeeee-8M-eeeee-8-eee (88, M8 = MM8); Meeeeee Meeeeeeee:[88]
M eeee ee 8-(8-eeeeeeeeeeee)-8-eeeeee-8,8-eeeeeee-8M-eeeee-8-eee (88, M8 = MM8; 888 ee, 8.88 eeee) ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeeee ee e eeeeee eeee eee 88 e. Meeee eeeeeee ee ee, eee eeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8); eeeee: 88 ee (88%); ee 888–888°M.
References
[17] | Meeeeeeeee, M.; Meeeeeeeee, M.; Meeeeeeeee, M., M. Meeeeeeee. Meeeeeeee., M, (8888) 88, 888. |
[18] | Meeeee, M.-M.; Me Meeeee, M.; Meeeeeee, M.-M., Meeeeeeeeee, (8888) 88, 8888. |
[19] | Meeeeeee, M. M.; Meeeee, M.; Meeeeeee, M., Mee. Meee., (8888) 8, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e8, 888.
- 8.Meeeee-Meee, (8888) 8/8e8, 888.