Water → HCID 13499466, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3,5-di-tert-butyldimethylsilyloxybenzoate (170 g, 0.429 mole) was dissolved in ether (800 ml) and cooled to 10° C. Lithium aluminum hydride (14.2 g, 0.374 mole) was added in small portions. After 0.5 h TLC revealed complete conversion (dichloromethane:methanol 95:5), and water (20 ml) was added dropwise to destroy the excess of lithium aluminum hydride. Water/formic acid 4:1 (500 ml) was added to dissolve the aluminum salts, the organic layer was separated, and the aqueous layer was extracted with ether. The combined ether layers were washed with 0.4M sodium hydroxide, water, and brine. After drying (sodium sulfate), the ether was removed in vacuo to yield 147 g of the benzyl alcohol (0.399 mole, 93%).

Provenance & Evidence