4-Oxo-4-(4'-trifluoromethyl-biphenyl-4-yl)-butyric acid, methyl ester → 4-Oxo-4-(4'-trifluoromethyl-biphenyl-4-yl)-butyric acid

HRID 1979168

Reaction equation

HRID 1979168 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:3][CH2:4][C:5]([O:7]C)=[O:6]>Cl>[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

3

Reactant 1

HCID 120568844-Oxo-4-(4'-trifluoromethyl-biphenyl-4-yl)-butyric acid, methyl ester

Product 1

HCID 230052404-Oxo-4-(4'-trifluoromethyl-biphenyl-4-yl)-butyric acidYield 99%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a manner similar to Example 4, Step (b), 4-oxo-4-(4′-trifluoromethyl-biphenyl-4-yl)-butyric acid, methyl ester (1.34 g, 0.00398 mol) was refluxed in 6 M aqueous hydrochloric acid (24 mL) to give 1.27 g of 4-oxo-4-(4′-trifluoromethyl-biphenyl-4-yl)-butyric acid as an 80% pure solid. A portion (0.059 g) of the material was purified by chromatography on silica gel (7 g, 230-400 mesh), eluting with dichloromethane (15×10 mL); dichloromethanemethanol (15:1; 16×10 mL) to give 0.0476 g of pure 4-oxo-4-(4′-trifluoromethyl-biphenyl-4-yl)-butyric acid as an off-white solid; mp 172-174° C.

Sources & evidence

ORD record
ord-014e80ec32204f6a8cc8350970e44ba7
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Linked notes

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