Reaction #56485

Reaction equation

hydrochloric acid

Sodium hydroxide

ethyl 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate

methanol

→

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

Solvents

water

water

Conditions

Workup

1. 1
   Extractionextracted with ether
2. 2
   ExtractionThe ethereal extract
3. 3
   Washis washed with water
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   TemperatureUpon cooling the filtrate
7. 7
   Otherthe title compound precipitates out as a white solid, which
8. 8
   Filtrationis collected by filtration (7.06 g., 2.57 mmol., 42%)
9. 9
   OtherThe product is recrystallized from chloroform-ether, m.p. 147°-148° C., ir (KBr) 3320, 1700, 1650 cm-1, pmr (CDCl3) δ3.54 (2H, s), 4.70 (1H, m), 7.22 (2H, d), 8.00 (2H, d)

Procedure

Sodium hydroxide solution (5 N, 2.5 ml., 12.5 mmol.) is added to a stirred mixture of ethyl 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate (2.48 g., 5.91 mmol.), methanol (25 ml.) and water (5 ml.). The resulting mixture is stirred at ambient temperature for 16 l hours. Then, it is diluted with water, acidified with diluted hydrochloric acid, and extracted with ether. The ethereal extract is washed with water, dried over anhydrous magnesium sulfate, and filtered. Upon cooling the filtrate, the title compound precipitates out as a white solid, which is collected by filtration (7.06 g., 2.57 mmol., 42%). The product is recrystallized from chloroform-ether, m.p. 147°-148° C., ir (KBr) 3320, 1700, 1650 cm-1, pmr (CDCl3) δ3.54 (2H, s), 4.70 (1H, m), 7.22 (2H, d), 8.00 (2H, d).

Source