Toluene → Retinol

HRID 2193861

Reaktionsgleichung

[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:21])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:20])=[CH:17]/[CH2:18][OH:19].C1(C)C=CC=CC=1.[C:29]([OH:49])(=[O:48])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39][C@@H:40]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[OH:41]>>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:21])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:20])=[CH:17]/[CH2:18][OH:19].[C:29]([O-:49])(=[O:48])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39][C@@H:40]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[OH:41]

Komponenten

Edukt 3

HCID 1140Toluene

HCID 445354Retinol

HCID 643684Ricinoleic Acid

Produkt 2

HCID 445354Retinol

HCID 25630959Ricinoleate

Versuchsvorschrift

To a vial was added retinol in toluene (54% retinol; 1.852 g; 1.0 g retinol; 3.49 mmol), ricinoleic acid (80%; 1.250 g; 4.19 mmol; 1.2 equiv), and Novozym 435 (1 g). The mixture was sealed and stirred at room temperature for 21 h to afford 83% conversion of retinol to 1b.

Aufarbeitung

customThe mixture was sealed

Quellen und Nachweise

ORD-Eintrag: ord-01292e060eeb485baa8e64f6fca7ff82
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08329938B2

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