Hydrochloric Acid → 6-Hydroxyhexanoic Acid

HRID 1799818Notes

Reaction equation

HRID 1799818 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, 1 H).

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-ce3e52f4c64048559021e5580c2bb781
Source dataset
uspto-grants-2013_01
Patent number
US08344175B2

Reaction notes

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