Methanol → 1,3-Diacetoxyacetone

HRID 2256464Notes

Reaction equation

HRID 2256464 reaction equation
C1O[C:5]([OH:9])([CH2:7][OH:8])[CH2:4][O:3][C:2]1([OH:12])[CH2:10]O.[C:13](OC(=O)C)(=[O:15])[CH3:14].CO>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:13]([O:8][CH2:7][C:5]([CH2:4][O:3][C:2](=[O:12])[CH3:10])=[O:9])(=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 4180364Dihydroxyacetone dimer

Product 1

HCID 2434181,3-Diacetoxyacetone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Under an atmosphere of argon, 90 g of 1,3-dihydroxyacetone dimer and 250 mg of 4-(N,N-dimethylamino)pyridine were dissolved in 250 ml of pyridine. To the resulting solution, 225 ml of acetic anhydride was added dropwise at room temperature over 1 hour. After the resulting liquid was stirred at room temperature for 30 minutes, thereto was added 50 ml of methanol and the resulting liquid was further stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure and the residue was subjected to a recrystallization from ether-petroleum ether to give 190 g of the desired compound.

Workup

  1. stirringthe resulting liquid was further stirred at room temperature for 30 minutes
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was subjected to a recrystallization from ether-petroleum ether

Sources & evidence

ORD record
ord-5b79b1be89c74c0daa18abfa97e407ce
Source dataset
uspto-grants-1997_08
Patent number
US05654472

Reaction notes

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