Benzyl Bromide → Benzyl 2-hydroxystearate

HRID 489074

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 acatate 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 acatate
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-a8bb89d7b8f94103849074a5d5070bc5
Quelldatensatz: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06974802B2

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