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

HRID 1181217Notes

Reaction equation

HRID 1181217 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-d676613fc8ec4cf5a21162a5a8b8c6ff
Source dataset
uspto-grants-2007_10
Patent number
US07285543B2

Reaction notes

Loading…