beta-Phenylisovaleric acid → 3,3-Dimethyl-1-indanone

Participants

Reaction Steps

To a solution of 3-methyl-3-phenyl butanoic acid (17.1 g, 95.5 mmoles) in benzene (70 mL) was added PCl5 (23.0 g, 0.11 mole, 1.15 eq.) portionwise with cooling. Upon completion of the addition, the reaction mixture was refluxed for 30 minutes and cooled to room temperature. Aluminum chloride (13.1 g, 98.3 mmoles) was added in increments and the reaction was heated at reflux for 30 minutes. The reaction mixture was poured onto ice; the oily layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with 5% HCl solution, saturated NaHCO3 solution, saturated NaCl solution and dried over MgSO4. The solvent was evaporated in vacuo and the crude product (14.3 g) was vacuum distilled (b.p.=103° C. @ 2.3 mmHg) to obtain 9.98 g of the title C compound as a colorless oil. MS: (M+H)+ @ 161.

Provenance & Evidence