Hydrochloric Acid → 6-Hydroxyhexanoic Acid

HRID 605444Notes

Reaction equation

HRID 605444 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-CAPROLACTONEHCID 14797Potassium Hydroxide

Product 1

HCID 144906-Hydroxyhexanoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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-a8a9cabd6aea49d386907d8f1deaf117
Source dataset
uspto-grants-2011_03
Patent number
US07914700B2

Reaction notes

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