Boron trifluoride etherate → 2-Nitrophenethyl alcohol

Participants

Reaction Conditions

Reaction Steps

A 22-liter, 4-necked glass reaction vessel equipped as described in Example 1 was charged with 624 grams (15.8 moles plus 5% excess) of sodium borohydride and 3620 grams (20 moles) of o-nitrophenylacetic acid and flushed for 0.5 hour with dry nitrogen. The reaction vessel was cooled to 0°C using an external dry ice/isopropyl alcohol bath as 10 liters of tetrahydrofuran was added dropwise over a 2 hour period. Boron trifluoride diethyl etherate (2.58 liters, 21 moles) was then added dropwise over a 4 hour period while maintaining a reaction temperature of 0°-10°C. The reaction mixture was then stirred for 12 hours at 20°-25°C. Isolation of the product as described in Example 1 gave 2450 grams (73% yield) of o-nitrophenethyl alcohol as a clear, light-orange liquid, bp 112°C/0.15 mm, n20D 1.5644.

Provenance & Evidence