Boron trifluoride etherate → 3-Phenoxybenzyl alcohol

Participants

Reaction Conditions

Reaction Steps

A 500-milliliter, 4-necked glass reaction vessel equipped with a magnetic stirring bar, pressure-equalizing addition funnel, thermometer, and reflux condenser vented to a mercury bubbler was charged with 9.6 grams (0.248 mole plus 5% excess) of sodium borohydride and 64 grams (0.30 mole) of m-phenoxybenzoic acid and flushed 10 minutes with dry nitrogen. The reaction vessel was cooled in an external ice/water bath as 0.2 liter of tetrahydrofuran was added dropwise followed by 40.6 milliliters (0.33 mole) of boron trifluoride diethyl etherate over a 1 hour period while maintaining a temperature of 0°-10°C. The reaction mixture was then stirred for 12 hours at 20°C followed by 2 hours at 40°C. The product was isolated using a procedure similar to that described in Example 1 giving 48 grams (80% yield) of m-phenoxybenzyl alcohol, n20D 1.5935.

Provenance & Evidence