Acetic Acid → 2,2-Diacetoxyacetyl chloride

HRID 1398946Notes

Reaction equation

HRID 1398946 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=[O:4].C(O[C:11](=[O:13])[CH3:12])(=O)C.[C:14]([OH:17])(=O)[CH3:15].S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[C:14]([O:5][CH:2]([O:6][C:11](=[O:13])[CH3:12])[C:3]([Cl:20])=[O:4])(=[O:17])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 24386Thionyl ChlorideHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 116513132,2-Diacetoxyacetyl chlorideYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of glyoxylic acid monohydrate (53.2 g, 578 mmol), acetic anhydride (530 mL, 5.61 mol) and acetic acid (120 mL) was refluxed for 2 h, concentrated in vacuo and azeotroped with toluene. The residue was diluted with toluene (270 mL), and thionyl chloride (84 mL, 1.15 mol) was added to the mixture. The resultant mixture was stirred at 60° C. for 16 h and concentrated in vacuo. The residue was purified by distillation (6-8 hpa, 70-80° C.) to afford compound the title compound as a colorless oil (70.7 g, 363 mmol, 63%).

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationconcentrated in vacuo
  3. customazeotroped with toluene
  4. additionwas added to the mixture
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was purified by distillation (6-8 hpa, 70-80° C.)

Sources & evidence

ORD record
ord-4b664ec0d070431a957f3b578210c0ed
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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