Phenyl chloroformate → 1,3-O-diphenyloxycarbonyl-2-O-methylglycerol

HRID 2260187Notes

Reaction equation

HRID 2260187 reaction equation
[CH3:1][O:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[C:8](Cl)(=[O:16])[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[OH2:19]>N1C=CC=CC=1>[C:10]1([O:9][C:8]([O:5][CH2:4][CH:3]([CH2:6][O:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:19])[O:2][CH3:1])=[O:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 111709312-Methoxypropane-1,3-diolHCID 21885828Hydrate;hydrochloride

Product 1

HCID 189999891,3-O-diphenyloxycarbonyl-2-O-methylglycerol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20 g of 2-methoxy-1,3-propanediol was dissolved in 200 ml of pyridine. 52.6 ml of phenyl chlorocarbonate was added dropwise to the solution under stirring and under cooling with ice. After two hours, the reaction solution was added to 1 l of 4N hydrochloric acid/water. After extraction with ether, the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, concentrated and purified according to silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 52 g of the intended product.

Workup

  1. temperatureunder cooling with ice
  2. extractionAfter extraction with ether
  3. washthe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-330d3a2bf28b4c799e6d27dc01316432
Source dataset
uspto-grants-1995_12
Patent number
US05476863

Reaction notes

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