Benzaldehyde → 1-Phenylbut-3-en-1-ol

To 0.30 ml (1.0 mmol) of tetraisopropoxytitanium and 5 ml of ethyl ether solution containing allyl bromide (1.0 mmol) was added dropwise at −50° C. 1.67 ml of 1.2M ethyl ether solution containing isopropylmagnesium bromide (2.0 mmol). Upon stirring at −50° C. to −40° C. for 1 hour, the reaction liquid turned from yellow into brown. To the reaction liquid was added 0.071 ml (0.7 mmol) of benzaldehyde at −45° C. to −40° C. The temperature was raised to −10° C. to 0° C. over 30 minutes. With 5 ml of 1N 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 97 mg of 1-phenyl-3-buten-1-ol (94% yields based on benzaldehyde).

1. additionwas added dropwise at −50° C
2. customthe reaction liquid
3. customTo the reaction liquid
4. temperatureThe temperature was raised to −10° C. to 0° C. over 30 minutes
5. customseparated into layers
6. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
7. dry with materialAfter drying with anhydrous magnesium sulfate
8. distillationthe solution was freed of solvent by vacuum distillation
9. customThe residues were purified by silica gel chromatography

ORD record

ord-da80cfd320f547a29825db22460bf3d6

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06867161B1