Benzaldehyde → 1-Phenylbut-3-en-1-ol

1.94 ml of a 1.4-molar solution of n-butyllithium (2.71 mmol) in pentane were added dropwise at 0° C. under argon for 2 min to a stirred solution of 500 mg (2.71 mmol) 3-tert-butyl-2,2-dimethylhex-5-en-3-ol in 4 ml THF. The solution obtained was stirred for 15 minutes, and then a solution of 610 mg (2.71 mmol) ZnBr2 in 2 ml THF and subsequently 275 μl (2.71 mmol) benzaldehyde were added. The reaction mixture was stirred for 1 hour and heated to room temperature. Subsequently, 15 ml NH4Cl solution were added. The organic components were extracted three times with 15 ml Et2O each, the combined organic phases were washed with 10 ml brine, then dried and concentrated under reduced pressure. The raw product obtained was cleaned by means of a silica column with 15% diethyl ether/light gasoline. There was obtained the alcohol as a colorless oil.

1. customThe solution obtained
2. stirringThe reaction mixture was stirred for 1 hour
3. extractionThe organic components were extracted three times with 15 ml Et2O each, the combined organic phases
4. washwere washed with 10 ml brine
5. customdried
6. concentrationconcentrated under reduced pressure
7. customThe raw product obtained

ORD record

ord-2ceeeff93e884a41af3a216084046c1a

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06291713B1