Benzene → Benzenepropanol, gamma-methyl-

Temperature

5 °C

A reaction vessel was fitted with a mechanical stirrer, thermometer and a reflux condenser capped with an additional funnel. While under a positive flow of dry nitrogen, the system was flame dried. The vessel was charged 250 ml of benzene and then 25 gm of aluminum chloride was added as quickly as possible. This mixture was cooled with stirring to 5° C. in an ice/salt bath and a solution of 7.2 gm (0.1 mol) of crotyl alcohol in 45 ml of benzene was added dropwise while maintaining the temperature below 5° C. Next, 50 ml of concentrated hydrochloric acid was added cautiously. After warming to room temperature, 50 ml of water was added and the lower organic phase removed. The aqueous portion was then extracted with benzene. The combined organics were washed with aqueous 10% sodium bicarbonate and water. After drying over anhydrous magnesium sulfate, filtering and evaporating, a dark oil was recovered. This was vacuum distilled to give 8.2 gm of colorless 3-phenyl butanol (ND25 = 1.5210).

1. customA reaction vessel was fitted with a mechanical stirrer
2. customthermometer and a reflux condenser capped with an additional funnel
3. temperatureWhile under a positive flow of dry nitrogen, the system was flame
4. customdried
5. additionThe vessel was charged 250 ml of benzene
6. addition25 gm of aluminum chloride was added as quickly as possible
7. temperatureThis mixture was cooled
8. temperaturewhile maintaining the temperature below 5° C
9. temperatureAfter warming to room temperature
10. customthe lower organic phase removed
11. extractionThe aqueous portion was then extracted with benzene
12. washThe combined organics were washed with aqueous 10% sodium bicarbonate and water
13. dry with materialAfter drying over anhydrous magnesium sulfate
14. filtrationfiltering
15. customevaporating
16. customa dark oil was recovered
17. distillationThis was vacuum distilled

ORD record

ord-2360c6cd338b4de5bc51a5ea71fbc888

Source dataset

uspto-grants-1977_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04022814