Sodium Sulfate → (R)-(+)-4-tert. butoxy-3-methyl-1-butanol

Participants

Reaction Steps

A slurry of 1.51 g. (0.0398 mole) of lithium aluminum hydride in 50 ml. of ether was stirred and cooled while a solution of 3.45 g. (0.0198 mole) of (R)-(+)-4-tert. butoxy-3-methylbutyric acid in 50 ml. of ether was added dropwise. After the addition was complete , the reaction mixture was stirred room temperature for 2 hours then cooled to 0° C. and cautiously decomposed 5.4 ml. saturated aqueous Na2SO4 solution. After stirring at room temperature for 18 hours, the mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product (3.05 g.) was chromatographed on 10 of silica gel. Elution with 2:1 parts by volume, 1:1 parts by volume and 1:2 parts by volume hexane-ether followed by evaporative distillation gave 2.68 (85%) of the (R)-(+)-4-tert. butoxy-3-methyl-1-butanol as a colorless liquid b.p. 100°-102° C. (bath temperature) (20 mm Hg.); [α]25D + 12.79° (c 2.19, C6H6).

Provenance & Evidence