Hydrochloric Acid → Benzoic acid, 4-(3-hydroxypropyl)-

Participants

Reaction Conditions

Reaction Steps

1.7M n-butyllithium in hexane (19.4 ml, 33 mmole) was added dropwise to a chilled (-78° C.) and stirred solution of diisopropylamine (4.63 ml, 33 mmole) in 20 ml of dry tetrahydrofuran (hereinafter THF). After 20 minutes, a solution of p-toluic acid (2.042 g, 15 mmole) in 20 ml of dry THF was added dropwise. After stirring at -78° C. for another 1.5 hours, 4 ml of HMPA was added followed immediately by a solution of ethylene oxide (2.99 g, 67.9 mmole) in 10 ml of dry THF. The resulting solution was stirred at -78° C. for 2 hours, treated with 5% hydrochloric acid and warmed up to room temperature, the THF being removed in vacuo. The aqueous solution was saturated with sodium chloride and extracted three times with ethyl ether. The combined ether extracts were concentrated from 300 to 100 ml and extracted with a 0.5N sodium hydroxide solution. This extract was acidified with 10% hydrochloric acid and extracted three times with ethyl ether. The ether extracts were dried over anhydrous magnesium sulfate and evaporated to a residue. This residue was chromatographed on a silica gel column, eluting successively with dichloromethane-ethyl acetate (9:1 and 1:1), ethyl acetate and dichloromethane-methanol (9:1) to give 750 mg of the title A compound, with consistent spectral data.

Provenance & Evidence