3-Phenoxybenzyl alcohol → m-Phenoxybenzyl 4-(2-fluorophenyl)-2-isopropyl-3-butenoate
Reaction equation
FC1C=CC=CC=1CC=O.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=[CH:19][CH:20]([CH:24]([CH3:26])[CH3:25])[C:21]([OH:23])=[O:22].[O:27]([C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37]O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=[CH:19][CH:20]([CH:24]([CH3:26])[CH3:25])[C:21]([O:23][CH2:37][C:36]1[CH:39]=[CH:40][CH:41]=[C:34]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:35]=1)=[O:22]Participants
4
Procedure
2-Fluorophenylacetaldehyde is converted into ethyl 4-(2-fluorophenyl)-4-isopropyl-3-butanoate and hydrolyzed to the acid using the procedure of Example 9. The acid, 4-(2-fluorophenyl)-2-isopropyl-3-butenoic acid, is reacted, via the acid chloride, with m-phenoxybenzyl alcohol to yield m-phenoxybenzyl 4-(2-fluorophenyl)-2-isopropyl-3-butenoate, MS m/e 404.3 (M+). 2-Fluorophenylacetaldehyde is prepared from o-fluoro-β-methoxystyrene via the dimethylacetal using the procedure of Winterfeldt, Berichte 96(12), 3349 (1963).
Sources & evidence
- ORD record
- ord-1ce98a526aa64b9f91dddc1d56aeeb66
- Source dataset
- uspto-grants-1981_05
- Patent number
- US04267359
Reaction notes
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