p-METHYLACETOPHENONE → 4,4,4-Trifluoro-1-(4-methylphenyl)butane-1,3-dione

HRID 2240471Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C([O:13][C:14](=O)[C:15]([F:18])([F:17])[F:16])C>>[F:16][C:15]([F:18])([F:17])[C:14](=[O:13])[CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:10]

Participants

Reactant 2

HCID 8500p-METHYLACETOPHENONE

HCID 9794Ethyl trifluoroacetate

Product 1

HCID 5501934,4,4-Trifluoro-1-(4-methylphenyl)butane-1,3-dione

Procedure

Claisen reaction of the commercially available p-methyl-acetophenone and trifluoroacetic acid ethyl ester gave 4,4,4-trifluoro-1-(4-methylphenyl)-butane-1,3-dione in good yield. The latter was further reacted with the commercially available p-hydrazino-benzenesulfonic acid in an inert solvent in the presence of hydrochloric acid to give the new 4-(5-p-methyl-phenyl)-3-trifluoromethyl-pyrazol-1-yl)-benzenesulfonic acid of formula (III) (yield over 80%),

Sources & evidence

ORD record: ord-b22d94fa4f424bfa997526ceea93fae6
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723370B2

Reaction notes

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