Reaction #543534

Reaction equation

acetate

4-(4-iodophenyl)butyric acid

potassium carbonate

2-hydroxythiophenol

→

4-(4-(2-hydroxyphenyl)thiophenyl)butyric acid

Solvents

dimethylformamide

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed for 18 hr
2. 2
   Temperaturecooled to 25 C
3. 3
   Extractionextracted with ethyl acetate
4. 4
   ConcentrationThe organic phase was concentrated
5. 5
   OtherThe residue was purified by flash chromatography

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.

Source