Acetic Anhydride → 2-Methyl-6-acetamidobenzyl alcohol

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][OH:5].[C:11](OC(=O)C)(=[O:13])[CH3:12].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([NH:1][C:11](=[O:13])[CH3:12])[C:3]=1[CH2:4][OH:5]

Participants

Procedure

To a suspension of 2-amino-6-methylbenzyl alcohol (30 g) in methylene chloride (300 ml) was added dropwise acetic anhydride (22.3 g) at 5° to 10° C. After being stirred for 3 hours, the mixture was neutralized with sodium bicarbonate aqueous solution to give precipitates. To said mixture was added chloroform to dissolve said precipitates and then the organic layer was washed with water and sodium chloride aqueous solution, dried over magnesium sulfate and evaporated in vacuo. The resultant residue was suspended in diethyl ether and the precipitates were collected by filtration to give 2-methyl-6-acetamidobenzyl alcohol (25.30 g).