Methyl glucoside → Dodecyl beta-D-glucopyranoside

HRID 619870Notes

Reaction equation

HRID 619870 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11]O)O)O)O)O.[CH3:13][O:14][C@H:15]1[O:20][CH:19]([CH2:21][OH:22])[C@H:18]([OH:23])[C@@H:17]([OH:24])[C@@H:16]1[OH:25]>>[CH3:2][CH2:3][CH2:5][CH2:7][CH2:9][CH2:11][CH2:2][CH2:3][CH2:5][CH2:7][CH2:9][CH2:13][O:14][C@@H:15]1[O:20][C@H:19]([CH2:21][OH:22])[C@@H:18]([OH:23])[C@H:17]([OH:24])[C@H:16]1[OH:25]

Participants

3

Reactant 2

HCID 76607Methyl glucosideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 93321Dodecyl beta-D-glucopyranoside

Conditions

Temperature
120 °C

Procedure

The insoluble material was filtered, washed with Skellysolve B® solvent, a hydrocarbon solvent boiling in the range of 60° to 70° C., and then dried by heating at 120° C. at a pressure of about 4 mm. mercury. The dry material, which had a mass of 20.15 g., was analyzed by liquid chromatography and was found to contain approximately 88 weight percent methyl polyglucoside. This corresponds to approximately 0.11 moles of glucose units using the following conversion: ##EQU1## Therefore, of the 0.14 moles of methyl glucoside initially present, approximately 0.11 moles (or 79 percent) formed methyl polyglucoside rather than the desired dodecyl glucoside.

Workup

  1. filtrationThe insoluble material was filtered
  2. washwashed with Skellysolve B® solvent
  3. customboiling in the range of 60° to 70° C.
  4. customdried

Sources & evidence

ORD record
ord-c73e2bba169f459694e990c1d04882b6
Source dataset
uspto-grants-1989_04
Patent number
USH0000619

Reaction notes

Loading…