4-Methylcyclohexanone → 6-Methyloxepan-2-one

HRID 241463Notes

Reaction equation

HRID 241463 reaction equation
[CH3:1][CH:2]1[CH2:7]C[C:5](=O)[CH2:4][CH2:3]1.[C:9](=[O:12])(O)[O-:10].[Na+].ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[CH3:1][CH:2]1[CH2:7][O:10][C:9](=[O:12])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 115254-MethylcyclohexanoneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 148667186-Methyloxepan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This was prepared in similar manner to Lactone 1 except using 4-methyl cyclohexanone (50 parts; 0.445m ex. Aldrich) in place of the 3-methylcyclohexanone with appropriate increase in the dichloromethane (1500 ml), sodium bicarbonate (8.1 parts, 1.0 M) and 3-chloroperoxybenzoic acid (123 parts; 0.5 M). The reaction temperature was maintained below 10° C. throughout. The 5-methyl ε-caprolactone was obtained as a clear yellow oil (49 parts).

Workup

  1. temperatureThe reaction temperature was maintained below 10° C. throughout

Sources & evidence

ORD record
ord-c930eece59f94ca5ab54d6442f1f2c42
Source dataset
uspto-grants-2014_02
Patent number
USRE044769E1

Reaction notes

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