1-Phenyl-1,2-propanedione → Dodecyl 3-hydroxy-2,2-dimethyl-4-oxo-3-phenylpentanoate

HRID 256134Notes

Reaction equation

HRID 256134 reaction equation
[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:19]1([C:25](=[O:29])[C:26](=[O:28])[CH3:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCCCCC>[OH:29][C:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:26](=[O:28])[CH3:27])[C:2]([CH3:3])([CH3:4])[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:5]

Participants

4

Reactant 2

HCID 113631-Phenyl-1,2-propanedioneHCID 243691Dodecyl isobutyrate

Product 1

HCID 20164021Dodecyl 3-hydroxy-2,2-dimethyl-4-oxo-3-phenylpentanoateYield 32%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The reaction of dodecyl isobutyrate (6.4 g, 0.025 mole) with 1-phenyl-1,2-propanedione (3.7 g, 0.025 mole) is conducted in the manner described in Example I. Thin layer chromatography of the crude reaction mixture indicated the presence of two main reaction products. High pressure liquid chromatography on silica gel using 2% ethyl acetate in hexane as the eluant yields pure dodecyl 3-hydroxy-2,2-dimethyl-4-oxo-3-phenylpentanoate (IVa) (3.2 g, 32%), b.p. 148° C. (Kugelrohr air bath temperature) at 0.005 mm Hg. Also recovered is pure dodecyl 3-hydroxy-2,2,3-trimethyl-4-oxo-4-phenylbutyrate (IVb) (3.5 g, 35%), b.p. 145° C. (Kugelrohr air bath temperature) at 0.005 mm Hg.

Workup

  1. customThin layer chromatography of the crude reaction mixture

Sources & evidence

ORD record
ord-23648e1391bb455c96a2132bba4afa02
Source dataset
uspto-grants-1987_10
Patent number
US04701282

Reaction notes

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