Water → 7-(2-Hydroxy-3,4,6-trimethylphenyl)-7-phenylheptanoic acid

HRID 2254350Notes

Reaction equation

[C:1]1([CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1O.CS(O)(=O)=O.[OH2:31]>ClCCl>[OH:31][C:18]1[C:17]([CH3:16])=[C:22]([CH3:23])[CH:21]=[C:20]([CH3:24])[C:19]=1[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

Conditions

Temperature: 25 °C

Procedure

7-Phenyl-6-heptenoic acid (10 g) and 2,3,5-trimethylphenol (8.3 g) were suspended in dichloromethane (80 ml). To the suspension was added dropwise methanesulfonic acid (9.4 g) at a temperature ranging from 17°-25° C. The mixture was stirred at 25° C. for 6 hours, to which was then added water (80 ml). The dichloromethane layer was separated and washed with water three times. Dichloromethane was distilled off under reduced pressure, and the residue was recrystallized from toluene (38 m;) to give 7-(2-hydroxy-3,4,6-trimethylphenyl)-7-phenylheptanoic acid (14.2g, 85.2%) as white crystals.

Workup

customranging from 17°-25° C
customThe dichloromethane layer was separated
washwashed with water three times
distillationDichloromethane was distilled off under reduced pressure
customthe residue was recrystallized from toluene (38 m;)

Sources & evidence

ORD record: ord-e69a5bd50ae546f3ad9e8375f5f95afc
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05235091

Reaction notes

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