alpha-Hydroxyacetophenone → 4,4-dimethyl-1-phenylpentane-1,3-dione

HRID 1647656Notes

Reaction equation

HRID 1647656 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:11][C:12]([CH3:18])([CH3:17])[C:13](NN)=[O:14]>>[C:12]([C:13]([CH2:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:4])=[O:14])([CH3:18])([CH3:17])[CH3:11]

Participants

3

Reactant 2

HCID 68490alpha-HydroxyacetophenoneHCID 5451472,2-Dimethylpropanehydrazide

Product 1

HCID 5899714,4-dimethyl-1-phenylpentane-1,3-dione

Procedure

The desired product is prepared as described in Example 1 using 2-hydroxyacetophenone (19.0 g, 140 mmol) and trimethylacetic hydrazide (10 g, 96 mmol). Yield: 5.0 g, 84%. m.p. 43°-45° C. 1H NMR (CDCl3), δ=1.25 (s, 9H, 3×CH3); 2.58 (s, 3H, CH3); 7.21 (d, 1H, ArH); 7.45-7.49 (m, 1H, ArH); 7.55-7.59 (m, 1H, ArH); 7.89 (d, 1H, ArH).

Sources & evidence

ORD record
ord-08518f4e1d2f4bc986413ffea0028edd
Source dataset
uspto-grants-1995_07
Patent number
US05433896

Reaction notes

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