Benzaldehyde → 1-Phenylbut-3-en-1-ol

Temperatur

0 °C

To 0.90 ml (3.0 mmol) of tetraisopropoxytitanium and 5 ml of n-butyl ether solution containing allyl bromide (3.0 mmol) was added dropwise at −78° C. 6.2 ml of 0.97M n-butyl ether solution containing isopropylmagnesium bromide (6.0 mmol). After stirring at −50° C. to −40° C. for 1 hour, the reaction liquid was given 0.21 ml (2.1 mmol) of benzaldehyde and heated to 0° C. over 30 minutes. With 10 ml of 3N hydrochloric acid added, the solution was heated to room temperature and separated into layers. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate. After drying with anhydrous magnesium sulfate, the solution was freed of solvent by vacuum distillation. The residues were purified by silica gel chromatography. Thus there was obtained 252 mg of 1-phenyl-3-buten-1-ol (81% yields based on benzaldehyde).

1. additionwas added dropwise at −78° C
2. customthe reaction liquid
3. temperaturethe solution was heated to room temperature
4. customseparated into layers
5. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
6. dry with materialAfter drying with anhydrous magnesium sulfate
7. distillationthe solution was freed of solvent by vacuum distillation
8. customThe residues were purified by silica gel chromatography

ORD-Eintrag

ord-011e1e4df19c46d5a267e3777b4ac4ce

Quelldatensatz

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06867161B1