Acetyl chloride → 2-(Acetyloxy)-5-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

1 g of 5-methylsalicylic acid (6.58 mmol) and 1.83 ml of tri-ethylamine (2 equivalents) were dissolved in 80 ml of ethyl acetate. At 0° C., 0.94 ml of acetyl chloride (2 equivalents) was added dropwise, and the mixture was then stirred at 23° C. for 1 h. The precipitated salts are [sic] filtered off. 100 ml of 1M HCl were added to the filtrate, which was then stirred overnight. A homogeneous solution formed, and it was adjusted to about pH 4 with saturated NaHCO3 solution. It was then extracted with chloroform, and the organic phase was washed with a little water and dried over MgSO4. The solvent was substantially removed, and the crude product was recrystallized from hexane/ethyl acetate.

Provenance & Evidence