Hydrochloric Acid → p-Tolyl isobutyrate

While stirring magnesium (22.5 g, 925 mmol) and iodine (1 crumb) in diethyl ether (400 ml), a solution of 4-methylbenzyl chloride (65.0 g, 463 mmol) in diethyl ether (500 ml) was dropwise added slowly at room temperature. After completion of the dropwise addition, the mixture was stirred at room temperature for 0.5 hr. To the reaction solution was added dropwise a solution of isobutyronitrile (21.31 g, 308.3 mmol) in diethyl ether (100 ml) under ice-cooling, and the mixture was stirred overnight at room temperature. To the reaction solution was added dropwise 1N hydrochloric acid under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The diethyl ether layer was separated from the mixture, and the aqueous layer was extracted with diethyl ether. The recovered organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1−9/1) to give the objective substance.

1. additionAfter completion of the dropwise addition
2. temperaturecooling
3. stirringthe mixture was stirred overnight at room temperature
4. temperaturecooling
5. stirringthe mixture was stirred at room temperature for 1 hr
6. customThe diethyl ether layer was separated from the mixture
7. extractionthe aqueous layer was extracted with diethyl ether
8. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
9. customThe solvent was evaporated under reduced pressure
10. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1−9/1)
11. customto give the objective substance

ORD record

ord-fc01ed19281b4a47a7761c9b5b4ef9ca

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2