Acetone → 2,2-Dimethyl-chroman-4-one

HRID 2249166Notes

Reaction equation

HRID 2249166 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].N1CCCC1.[CH3:16][C:17]([CH3:19])=[O:18]>>[CH3:16][C:17]1([CH3:19])[CH2:2][C:3](=[O:4])[C:5]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:18]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 74542902,2-Dimethyl-chroman-4-one

Procedure

The reaction of 2-hydroxyacetophenone with acetone in the presence of pyrrolidine analogously to Synthesis 886, 1978 gives 2,2-dimethyl-4-chromanone of melting point 80°-85° C. 2,2-Dimethyl-4-hydroxy-chroman (oil) is obtained from 2,2-dimethyl-4-chromanone by reduction using sodium borohydride in ethanol.

Workup

  1. customanalogously to Synthesis 886, 1978

Sources & evidence

ORD record
ord-770cc114459c4f0090d402244fa44bc9
Source dataset
uspto-grants-1991_08
Patent number
US05043344

Reaction notes

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