Methyl chloroformate → 3-Hydroxy-2-(hydroxymethyl)propyl methyl carbonate

HRID 1063779Notes

Reaction equation

HRID 1063779 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].Cl[C:9]([O:11][CH3:12])=[O:10]>ClCCl.N1C=CC=CC=1>[CH3:12][O:11][C:9]([O:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5])=[O:10]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 78432Trimethylolmethane

Product 1

HCID 222749913-Hydroxy-2-(hydroxymethyl)propyl methyl carbonateYield 42.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(hydroxymethyl)-1,3-propanediol (9.4 mmol) in dichloromethane (20 mL) and pyridine (7.5 mL) at 0° C. was added methyl chloroformate (9.4 mmol) slowly. The resulting solution was warmed to room temperature and stirred for 16 h. The reaction was concentrated under reduced pressure and chromatographed by eluting with methanol-dichloromethane (1:4) to give 650 mg of 2-(methoxycarbonyloxymethyl)-1,3-propanediol.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customchromatographed
  3. washby eluting with methanol-dichloromethane (1:4)

Sources & evidence

ORD record
ord-0cb922e91b3c4a93b04716b1e583a6e2
Source dataset
uspto-grants-2005_11
Patent number
US06967193B1

Reaction notes

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