Methyl p-toluenesulfonate → 1-Propanone, 2-methoxy-1,2-diphenyl-

HRID 1578545Notes

Reaction equation

HRID 1578545 reaction equation
[CH3:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([OH:11])[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:18]OS(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>CS(C)=O>[CH3:18][O:11][C:2]([CH3:1])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 14798Sodium HydroxideHCID 3446932-hydroxy-1,2-diphenyl-1-propanone

Product 1

HCID 35415691-Propanone, 2-methoxy-1,2-diphenyl-Yield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5.7 g (2.5 . 10-2 mol) α-methyl-benzoin are reacted in 50 ml DMSO at room temperature with 5 g (2.8 . 10-2 mol) p-toluene-sulphonic acid methyl ester in the presence of 11 ml of a 10% by weight sodium hydroxide solution. The crude product is filtered through silica gel/petroleum ether and yields, besides 0.95 g (17% of theory) of educt, 4.8 g (80% of theory) α-methyl-benzoin methyl ether of m.p. 36° - 38°C (petroleum ether).

Workup

  1. filtrationThe crude product is filtered through silica gel/petroleum ether

Sources & evidence

ORD record
ord-2e0beafdf2704f67b759aa582eba9719
Source dataset
uspto-grants-1976_02
Patent number
US03937722

Reaction notes

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