Methanol → Hexanoic acid, 6-hydroxy-, methyl ester

HRID 9800Notes

Reaction equation

HRID 9800 reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.OS(O)(=O)=O.[CH3:14][OH:15]>>[CH3:14][O:15][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 10401epsilon-CAPROLACTONE

Product 1

HCID 3083855Hexanoic acid, 6-hydroxy-, methyl ester

Procedure

A solution of ε-caprolactone (11.4 g, 0.100 mol), MeOH (300 mL) and concentrated H2SO4 (5 mL) was refluxed overnight. The resulting mixture was cooled to room temperature and concentrated. Water was added to the residue and the pH was adjusted to 7 with solid NaHCO3. The aqueous layer was extracted with ether. The combined organic layers were washed with water, dried and concentrated to give 6-hydroxy-hexanoic acid methyl ester as a colorless oil, which was used in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. additionWater was added to the residue
  3. extractionThe aqueous layer was extracted with ether
  4. washThe combined organic layers were washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aade5df588aa4d7984bc144871052427
Source dataset
uspto-grants-2006_08
Patent number
US07091357B2

Reaction notes

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