Diethyl Ether → Acetoxymethyl glycolate

HRID 2379264Notes

Reaction equation

HRID 2379264 reaction equation
[C:1]([O-:5])(=[O:4])[CH2:2][OH:3].[K+].[C:7]([O:10][CH2:11]Br)(=[O:9])[CH3:8].C(OCC)C>C(#N)C>[C:1]([O:5][CH2:11][O:10][C:7](=[O:9])[CH3:8])(=[O:4])[CH2:2][OH:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 68536Bromomethyl acetateHCID 23668515Potassium Glycolate

Product 1

HCID 18958287Acetoxymethyl glycolateYield 54.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of potassium glycolate (11.4 g) in acetonitrile (30 ml) KI (0.5 g) and acetoxymethyl bromide (19 g) were added. The mixture was stirred at 50° C. for 6 hours, and then cooled to room temperature. Diethyl ether was added and the solid filtered off. The solution was evaporated in vacuo and the oily residue was purified by column chromatography to yield 8 g of acetoxymethyl glycolate as a colourless oil.

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. filtrationthe solid filtered off
  4. customThe solution was evaporated in vacuo
  5. customthe oily residue was purified by column chromatography

Sources & evidence

ORD record
ord-d44cee9c70c04fc49d49546f1dd8d267
Source dataset
uspto-grants-1994_11
Patent number
US05360904

Reaction notes

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