Sulfuric Acid → 3-Benzyl-2-cyclohepten-1-one

Participants

Reaction Steps

A solution of 3-ethoxy-2-cyclohepten-1-one(5 g, 0.89 mol) in THF (70 mL) was added at room temperature to a solution of 2M benzyl magnesium chloride (800 ml) under N2 and stirred for 6 h. The resulting mixture was poured into a solution of 30% H2SO4 and stirred for 5 h. The resulting organic layer was separated, and the aqueous layer was extracted with several portions of ether. The combined organic layer was dried (MgSO4), and concentrated in vacuo to give 3-benzyl-2-cyclohepten-1-one (3.1 g, 65%) as a colorless oil. NMR (CDCl3); 3.45(s,2H1benzylic protons), 5.97 (bs, 1H, olefinic proton), 7.22 (m, 5H, aromatic protons).

Provenance & Evidence