Phenylacetaldehyde → 2-Phenylethanol

Temperature

85 °C

Anhydrous isopropyl alcohol, 406 grams, aqueous potassium hydroxide, 60 grams of a 4 percent solution, and 1 gram of 3 percent palladium on carbon were charged to a 2-liter stainless steel autoclave. The autoclave was purged with hydrogen and heated to 85° C. The autoclave was pressurized to 1200 p.s.i.g. with hydrogen. Styrene oxide, 765 grams of 97 percent purity, was fed to the stirred autoclave over a 7-hour period at a uniform rate. Hydrogen pressure was maintained at 1100 to 1200 p.s.i.g. by alternately adding fresh hydrogen. Immediately after the adddition of styrene oxide, the reaction mixture was cooled to ambient temperature and analyzed by gas chromatography using an internal standard. The yield 2-phenylethanol was 92.2 percent based on a styrene oxide purity of 97.0 percent. The unrefined reaction mixture contained 1.12 l weight percent phenylacetaldehyde and 0.7 weight percent phenylpropanol-2. A portion of the reaction mixture, 1060 grams, was distilled to give 580 grams of 97.8 percent 2-phenylethanol. This is equivalent to 88.16 percent of the theoretical 2-phenylethanol and a recovery efficiency based on the gas chromatographic analysis of the unrefined product of 95.62 percent.

1. customThe autoclave was purged with hydrogen
2. waitStyrene oxide, 765 grams of 97 percent purity, was fed to the stirred autoclave over a 7-hour period at a uniform rate
3. temperatureHydrogen pressure was maintained at 1100 to 1200 p.s.i.g
4. additionby alternately adding fresh hydrogen
5. temperatureImmediately after the adddition of styrene oxide, the reaction mixture was cooled to ambient temperature
6. customThe unrefined reaction mixture
7. distillationA portion of the reaction mixture, 1060 grams, was distilled

ORD record

ord-54e3fc3138d444bc8f02a8140a462806

Source dataset

uspto-grants-1977_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04064186