Hydrochloric Acid → 6-Hydroxyhexanoic Acid

HRID 1095208Notes

Reaction equation

HRID 1095208 reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:9].[K+].CO.Cl>C1COCC1>[OH:9][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10401epsilon-CAPROLACTONE2×HCID 14797Potassium Hydroxide

Product 1

HCID 144906-Hydroxyhexanoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 10 was first made 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).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6259e7470c134c3e90fc851ea2a36cab
Source dataset
uspto-grants-2012_03
Patent number
US08137582B2

Reaction notes

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