epsilon-CAPROLACTONE → Hexanoic acid, 6-hydroxy-, methyl ester

HRID 2292479Notes

Reaction equation

HRID 2292479 reaction equation
[CH2:1]1[CH2:8][CH2:7][O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[C:9](=O)([O-])[O-:10].[K+].[K+]>CO>[CH3:9][O:10][C:4](=[O:5])[CH2:3][CH2:2][CH2:1][CH2:8][CH2:7][OH:6]

Participants

4

Reactant 2

HCID 10401epsilon-CAPROLACTONEHCID 11430Potassium Carbonate

Product 1

HCID 3083855Hexanoic acid, 6-hydroxy-, methyl esterYield 556.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 10.6 ml (0.1 mol) e-caprolactone and 1.97 g (0.015 mol) potassium carbonate in 50 ml methanol is stirred for one hour at room temperature, then the potassium carbonate is removed by filtration and the mother liquor is evaporated to dryness in a vacuum. The residue is taken up in 20 ml saturated ammonium chloride solution and the solution is extracted three times with 50 ml diethyl ether each time. After drying the combined organic phases over sodium sulfate and removing the solvent, 12.2 g 6-hydroxycaproic acid methyl ester is obtained which is reacted further without additional purification.

Workup

  1. customthe potassium carbonate is removed by filtration
  2. customthe mother liquor is evaporated to dryness in a vacuum
  3. extractionthe solution is extracted three times with 50 ml diethyl ether each time
  4. dry with materialAfter drying the combined organic phases over sodium sulfate
  5. customremoving the solvent

Sources & evidence

ORD record
ord-5196e70f460d446f85bc369ec4bee78e
Source dataset
uspto-grants-1997_11
Patent number
US05683994

Reaction notes

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