Benzyl Bromide → Benzyl 2-hydroxystearate

HRID 1170664

Reaktionsgleichung

[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]([OH:5])=[O:4].CC(C)([O-])C.[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]([O:5][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a stirred solution of DL-2-hydroxystearic acid (3.0 g, 10 mmole) in 20 ml dry DMF was added potassium tert-butoxide (1.23 g, 11 mmole) and the mixture was stirred for one hour at 60° C. Benzyl bromide (2.14 g, 12.5 mmole) was added and the mixture was stirred for six hours at 80° C. The mixture was evaporated under reduced pressure and 100 ml ethyl acetate was added. The organic phase was separated and washed four times with water. The organic phase was dried with sodium sulfate and concentrated in vacuo. The product was isolated by silica gel column chromatography. Yield: 3.3 g

Aufarbeitung

stirringthe mixture was stirred for six hours at 80° C
customThe mixture was evaporated under reduced pressure and 100 ml ethyl acetate
additionwas added
customThe organic phase was separated
washwashed four times with water
dry with materialThe organic phase was dried with sodium sulfate
concentrationconcentrated in vacuo
customThe product was isolated by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-19aef74856e4452fbdd44fc7c950a12c
Quelldatensatz: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07825238B2

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