Methanol → HCID 20059823, compound

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][C:17]([O:19]CC2C=CC=CC=2)=[O:18])=[C:11]([CH3:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+]>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:27])[C:12]([CH2:16][C:17]([OH:19])=[O:18])=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

0.35 g of benzyl 2-(4-benzyloxy-2,6-dimethylphenyl)acetate was shaken overnight with a mixture of 7 ml of methanol, 0.7 ml of water and 0.28 g of solid sodium hydroxide. The resulting solution was evaporated and the residue was partitioned between 50 ml of methylene chloride and 25 ml of 2M hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and evaporated. The solid residue was recrystallized from a mixture of 3 ml of methanol and 3 ml of water to give 0.21 g of 2-(4-benzyloxy-2,6-dimethylphenyl)acetic acid of melting point 149°-150° C.