Acetate → 4-(4-(2-Hydroxyphenyl)thiophenyl)butyric acid

HRID 19441

Reaction equation

HRID 19441 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[SH:27].C([O-])(=O)C>CN(C)C=O>[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 175AcetateHCID 11430Potassium CarbonateHCID 70718Phenol, o-mercapto-(6CI,7CI,8CI)HCID 46454274-(p-Iodophenyl)butyric acid

Product 1

HCID 684943804-(4-(2-Hydroxyphenyl)thiophenyl)butyric acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-iodophenyl)butyric acid (0.86M) and dimethylformamide was treated with 2 eq of potassium carbonate, 1.5 eq of 2-hydroxythiophenol and a catalytic amount of cuperic acetate (0.01 eq). The reaction mixture was refluxed for 18 hr, cooled to 25 C, acidified with aqueous acid and extracted with ethyl acetate. The organic phase was concentrated. The residue was purified by flash chromatography using ethyl acetate/hexane as eluant to give 4-(4-(2-hydroxyphenyl)thiophenyl)butyric acid.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hr
  2. temperaturecooled to 25 C
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase was concentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e7e01cb1d6b341e290203e4523dd3350
Source dataset
uspto-grants-2010_06
Patent number
US07744910B2

Linked notes

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