Acetic Acid → 2-[2-(Dimethylamino)phenyl]-1,1-diphenylethanol

In a 30 ml Schlenk flask, 0.514 g (3.80 mmol) of N,N-dimethyl-o-toluidine, 0.898 g (7.60 mmol) of α-methylstyrene, 6.60 g of hexane and 4.43 ml (38.0 mmol) of cyclopentyl methyl ether were placed. Then, 4.78 ml (7.60 mmol) of a 1.59M n-butyllithium hexane solution was dropwise added at 25° C., and the mixture was stirred for 13 hours. To the reaction mixture, a diethyl ether solution containing 1.34 g (7.50 mmol) of benzophenone was dropwise added, and the mixture was stirred for 30 minutes. The resulting reaction mixture was added to a diethyl ether solution containing 0.500 g (8.3 mmol) of acetic acid, and the mixture was stirred for 5 minutes. Thereafter, 5 ml of water was added, and the mixture was further stirred for 5 minutes. After the aqueous phase was separated, the organic phase was extracted with 10% hydrochloric acid, and the resulting aqueous phase was neutralized, whereby 2-(2-(dimethylamino)phenyl)-1,1-diphenylethanol was obtained as a white crystal. The yield was 0.680 g and was 56%. Identification was carried out by a 1H-NMR spectrum. The results of the measurement are given below.

1. additionwas dropwise added
2. stirringthe mixture was stirred for 30 minutes
3. customThe resulting reaction mixture
4. stirringthe mixture was stirred for 5 minutes
5. stirringthe mixture was further stirred for 5 minutes
6. customAfter the aqueous phase was separated
7. extractionthe organic phase was extracted with 10% hydrochloric acid

ORD-Eintrag

ord-4cf1b9966d294075a784c97bb18b594b

Quelldatensatz

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08409480B2