Dimethyl Sulfide → Cyclopentanepropanol

Participants

Reaction Steps

A 12-liter, 4-necked glass reaction vessel equipped as described in Example 1 was charged with 180 grams (4.75 moles) of sodium borohydride, 4 liters of tetrahydrofuran, 0.485 liter (6.6 moles) of dimethyl sulfide, and 0.74 liter (6.0 moles) of boron trifluoride diethyl etherate at 0°-5°C using essentially the same procedure as described in Example 1. After stirring for a additional 0.5 hour at 20°-25°C, 780 grams (5.5 moles) of 3-cyclopentylpropionic acid was added dropwise over a 3 hour period while maintaining a temperature of 35°-40°C. After standing overnight at room temperature, hydrolysis of the reaction mixture followed by distillation of the crude product gave 613 grams (87.5% yield) of 3-cyclopentyl-1-propanol, bp 93°-95°C at 8 mm, n20D 1.4595.

Provenance & Evidence