Reaction #2028896

Reaction equation

HCl

caprolactone

Caprolactone

potassium hydroxide

methanol

→

6-hydroxyhexanoic acid

Solvents

THF

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe combined organic layers were washed with water
3. 3
   Otherdried
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Procedure

First, the synthesis of Compound 20 was preformed following the procedure reported in PCT/JP2005/004389. 6-Hydroxyhexanoic acid was synthesized by base hydrolysis of caprolactone. Caprolactone (100 g) was added to a mixture of potassium hydroxide (145 g), methanol (110 mL), and THF (390 mL). The resulting mixture was stirred at room temperature overnight. The solution was then acidified with HCl and extracted with ethyl acetate. The combined organic layers were washed with water, dried, filtered, and concentrated to obtain 6-hydroxyhexanoic acid. 1H NMR (CDCl3, 500 MHz) δ 1.44 (m, 2H), 1.60 (m, 2H), 1.68 (m, 2H), 2.37 (t, J=7.5 Hz, 2H), 3.66 (t, J=6.5 Hz, 2H), 5.80 (br, 1H).

Source