Dimethyl Sulfoxide → 1,3-Bis(benzyloxy)propan-2-one

HRID 1645519Notes

Reaction equation

HRID 1645519 reaction equation
ClCCl.[CH2:4]([O:11][CH2:12][CH:13]([OH:23])[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.CS(C)=O>C(OCC)(=O)C.O>[CH2:4]([O:11][CH2:12][C:13]([CH2:14][O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:23])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 2476141,3-Bis(benzyloxy)propan-2-ol

Product 1

HCID 113915821,3-Bis(benzyloxy)propan-2-oneYield 100.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dichloromethane (200 ml) solution of 1,3 dibenzyloxy-2-propanol (52 g, 191 mmol), triethylamine (130 ml, 933 mmol), and dimethylsulfoxide (65 ml, 916 mmol), sulfur trioxide pyridine complex (131 g, 823 mmol) was added at 0° C. and stirred at 0° C. to room temperature for 2 hours. To the mixture, water and ethyl acetate were added. The organic layer was washed with 2N hydrochloric acid, water and an aqueous saline solution, dried over anhydrous sodium sulfate, and concentrated. As a result, the title compound (52.01 g, quantitative yield) was obtained as a brown oil.

Workup

  1. washThe organic layer was washed with 2N hydrochloric acid, water
  2. dry with materialan aqueous saline solution, dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-120c97dbd1a24c38809dbfdb7946abeb
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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