Sulfuric Acid → (1-Hydroxymethylcyclopropyl)acetic acid methyl ester

Participants

Reaction Steps

5 g 2-[1-(hydroxymethyl)cyclopropyl]acetic acid (compound (13)) was dissolved in 65 ml methanol and 80 mg sulfuric acid was added. The reaction mixture was stirred overnight at room temperature; reaction progress was monitored by GC. The pH of the reaction mixture was adjusted to 7 with saturated NaHCO3. The reaction mixture was evaporated to dryness. 75 ml of ethyl acetate and 10 ml brine were added. The water layer was washed with 20 ml ethyl acetate. The combined organic layers were dried (Na2SO4) and evaporated to dryness, resulting in a yellow oil.

Provenance & Evidence