Hydrochloric Acid → 4-[1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid

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Reaction Conditions

Reaction Steps

To a suspension of the ester 16 (94 mg, 0.27 mmol) in 75% aqueous methanol (2 mL) was added potassium hydroxide (0.045 g), and the reaction mixture was stirred at 50° C. for 14 h during which time the material dissolved. The solution was cooled to room temperature, acidified with 2N aqueous hydrochloric acid, and then extracted with ether. The combined organic layers were washed with water and brine. The organic solution was then dried over anhydrous MgSO4, filtered and concentrated to afford a white solid. Recrystallization from benzene-hexane afforded the desired acid 48 as a white crystalline solid (0.074 g, 82%): m.p. 201°-204° D. The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy.

Provenance & Evidence