Sulfuric Acid → (Z)-8-hydroxy-5-octenoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of 14.2 g (30 mmoles) of the 2-methoxy-2-propyl ether of (3-hydroxypropyl)triphenylphosphonium bromide in 150 ml of tetrahydrofuran and 30 ml of hexamethylphosphorictriamide was slowly added 19 ml of n-butyllithium (1.6 M in hexane), at -78° C., under argon. The solution quickly turned yellow in color. Without delay, 2.6 g (20 mmoles) of methyl 4-formylbutyrate in 30 ml of tetrahydrofuran was added, and the resulting mixture was stirred for 30 min. at -78° C., allowed to warm to room temperature, and then stirred for 1 hour at room temperature. To the reaction mixture was added 1 N H2SO4 solution (pH 1 to 2). After stirring for 1 hour at room temperature, the product was extracted with ether. The ether extracts were washed with brine, saturated aqueous NaHCO3, and brine, then dried over MgSO4 and concentrated under reduced pressure. The resultant oily material was chromatographed on silica gel to give 2.00 g (58.3%) of (Z)-8-hydroxy-5-octenoic acid methyl ester.

Provenance & Evidence