Methanol → 1,3-Diacetoxyacetone

HRID 356808Notes

Reaction equation

HRID 356808 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 droopowise 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-33d87c0372054796ae65535c31a4f149
Source dataset
uspto-grants-1998_11
Patent number
US05840553

Reaction notes

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