Ammonia → 4-Methylcyclohexanone

HRID 268196Notes

Reaction equation

HRID 268196 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.OO.[NH3:11].C[O-].[Na+]>CO>[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH3:1][CH:2]1[CH2:7][CH2:6][NH:11][C:5](=[O:8])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 115254-MethylcyclohexanoneHCID 10942334Sodium Methoxide

Product 2

HCID 115254-MethylcyclohexanoneHCID 137496Hexahydro-5-methyl-2H-azepin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4,4' -Dimethyl-1,1'-peroxydicyclohexylamine (5 g.) derived from the reaction of 4-methylcyclohexanone, hydrogen peroxide and ammonia) was added to a solution of sodium methoxide in methanol (1 g. of sodium in 20 c.c. methanol) and the mixture heated under reflux for 2 hours when very little peroxide remained unreacted. The product was worked up as in Example 17 to give, on distillation, 4-methylcyclohexanone (2.2 g.), 4-methyl-caprolactam (2.2 g.), b.p. 145°-150°/15 mm, and residue (0.3 g.). The structure of the lactam was confirmed by I.R. and N.M.R. spectra.

Workup

  1. temperaturethe mixture heated

Sources & evidence

ORD record
ord-7f6bcf16a54641539a20d66e3c3620cd
Source dataset
uspto-grants-1976_03
Patent number
US03947406

Reaction notes

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