Phenylacetaldehyde → alpha-Ethenylbenzeneethanol

Temperature

0 °C

A solution of phenylacetaldehyde(600 mg, 5 mmol) in 12 ml of tetrahydrofuran was added dropwise over about 10 minutes to a solution of vinyl magnesium bromide (10 ml; 1M in tetrahydrofuran; 10 mmol) in 12 ml of tetrahydrofuran at 0° C. The internal temperature was maintained below 5° C. during the addition. After stirring for 1 hour at 0° C., the reaction was quenched by adding about 25 ml of saturated ammonium chloride solution. The resulting mixture was extracted with 100 ml of ethyl ether. The organic layer was washed with saturated ammonium chloride solution(50 ml) and brine(50 ml). Drying over magnesium sulfate and concentrating afforded 750 mg of the title product as a light orange liquid.

1. temperatureThe internal temperature was maintained below 5° C. during the addition
2. customthe reaction was quenched
3. additionby adding about 25 ml of saturated ammonium chloride solution
4. extractionThe resulting mixture was extracted with 100 ml of ethyl ether
5. washThe organic layer was washed with saturated ammonium chloride solution(50 ml) and brine(50 ml)
6. dry with materialDrying over magnesium sulfate
7. concentrationconcentrating

ORD record

ord-40ed392c0d1e467b9d68eba3c3e5ba10

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05492910