Reaction #56487

Reaction equation

4-{3-[3-[2-(1-Cyclohexenyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid

sodium hydroxide

hydrochloric acid

→

4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

Solvents

trifluoroacetic acid

water

Conditions

Workup

1. 1
   OtherExcess trifluoroacetic acid is then removed by evaporation at reduced pressure
2. 2
   OtherThe title compound precipitates as a solid
3. 3
   OtherRecrystallization from acetonitrile-water
4. 4
   Otheryields the
5. 5
   Otherpurified title compound, m.p. 147°-148° C.

Procedure

A solution of 4-{3-[3-[2-(1-Cyclohexenyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (3.7 g., 0.01 mole) in trifluoroacetic acid (20 ml.) is allowed to stand at 25° C. for 4 hours. Excess trifluoroacetic acid is then removed by evaporation at reduced pressure. The oily residue is dissolved in a solution of sodium hydroxide (2.0 g., 0.05 mole) in water (40 ml.). The basic solution is acidified with 2 N hydrochloric acid. The title compound precipitates as a solid. Recrystallization from acetonitrile-water yields the purified title compound, m.p. 147°-148° C.

Source