Lauric Acid → 6-Lauroyl ethyl glucoside

HRID 1612911Notes

Reaction equation

HRID 1612911 reaction equation
[O:1]([CH2:13][CH3:14])[CH:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:15](O)(=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>>[C:15]([O:12][CH2:11][C@H:9]1[O:10][CH:2]([O:1][CH2:13][CH3:14])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])(=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

3

Reactant 2

HCID 3893Lauric AcidHCID 11127487Ethyl D-glucopyranoside

Product 1

HCID 111436406-Lauroyl ethyl glucosideYield 96.7%

Procedure

To a mixture of crude ethyl D-glucopyranoside (578 g, 2.78 mol, prepared according to example 10) and dodecanoic acid (751 g, 3.75 mol) in a stirred batch reactor at 70° C. was added immobilized lipase derived from Candida antarctica (29 g, prepared as described in Danish patent application No. 3250/88). Stirring was continued under reduced pressure (0.05 bar) and the progress of the ester synthesis was monitored by HPLC. After 23 hours the enzyme was removed by filtration (at 70° C.). Excess fatty acid was removed by repeated molecular distillation (105° C., 0.04 mbar) yielding 96% (1050 g) of crude product along with 2% ethyl D-glucoside and 2% of a mixture of diesters (HPLC analysis). The crude product was purified by chromatography Identification by 1H NMR-analysis showed a 1:1 mixture of α and β anomers (tables 42/46).

Workup

  1. additionwas added immobilized lipase
  2. customprepared
  3. customAfter 23 hours the enzyme was removed by filtration (at 70° C.)
  4. customExcess fatty acid was removed
  5. distillationdistillation (105° C., 0.04 mbar)

Sources & evidence

ORD record
ord-a4dabdfb4fd14c2e8ab9918e8f5d798b
Source dataset
uspto-grants-1993_03
Patent number
US05191071

Reaction notes

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