2-Methylcyclohexanone → HCID 5312788, compound

HRID 363517Notes

Reaction equation

HRID 363517 reaction equation
CC1CCCCC1=[O:8].Cl[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18]O)=[O:17])[CH:11]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[OH:8][CH:14]([CH3:13])[CH2:15][CH2:10][CH2:11][CH2:12][C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 114192-MethylcyclohexanoneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 5312788HCID 5312788, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 2-methylcyclohexanone (11.1 g, 0.099 mol) in chloroform (15 ml) was added during 20 minutes, under nitrogen, to a stirred suspension of m-chloroperbenzoic acid (24.6 g, 0.143 mol) in chloroform (250 ml). After 3 hours, 40 minutes, the mixture was poured into aqueous sodium bicarbonate and extracted with methylene chloride. The extract was washed with brine, dried (MgSO4) and concentrated. The residue was distilled from a small amount of K2CO3 to give 9.58 g, bp 78°-79° C. (2.5-3 mm Hg) of 6-hydroxyheptanoic acid, ε-lactone.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. distillationThe residue was distilled from a small amount of K2CO3

Sources & evidence

ORD record
ord-409cffbde00543d2bdd8aab580f28774
Source dataset
uspto-grants-1999_02
Patent number
US05874475

Reaction notes

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