Ethylene Glycol → Polyethylene glycol monolaurate

HRID 2294760

Reaction equation

HRID 2294760 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].CC(C)=O.[C:9](Cl)(=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>N1C=CC=CC=1>[OH:3][CH2:2][CH2:1][O:4][C:9](=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 180AcetoneHCID 8166Dodecanoyl chloride

Product 1

HCID 62699Polyethylene glycol monolaurateYield 95.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under cooling with ice, ethylene glycol (434 mg) was dissolved into acetone (20 ml), and pyridine (632 mg) was added thereto and then lauroyl chloride (1532 mg) was added dropwise thereto. The temperature of the solution was warmed to room temperature, and it was stirred for 2 hours. The mixture was evaporated. To the residue was added water, and the solution was extracted with ethyl acetate. The organic layer was washed with water (three times), dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (1.63 g) having the following physical data.

Workup

  1. additionwas added
  2. customThe mixture was evaporated
  3. additionTo the residue was added water
  4. extractionthe solution was extracted with ethyl acetate
  5. washThe organic layer was washed with water (three times)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-7d11efc8ffa84e98977b6dbc75123864
Source dataset
uspto-grants-1997_11
Patent number
US05690957

Linked notes

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