m-Chloroperbenzoic acid → HCID 13188178, compound

HRID 851330Notes

Reaction equation

HRID 851330 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1([CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=[O:23])C.[Na+].ClC1C=C(C=CC=1)C(OO)=O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1([CH3:20])[O:23][C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH2:18]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 517045Sodium AcetateHCID 13188177HCID 13188177, compound

Product 1

HCID 13188178HCID 13188178, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4'-benzyloxybutyl)-2-methylcyclohexanone (25.2 g, 0.092 mol), sodium acetate (8.2 g, 0.1 mol), m-chloroperoxybenzoic acid 85% (24.2 g, 0.12 mol) and distilled methylene chloride (1200 ml) is heated at reflux under a nitrogen atmosphere for 7 hours. The solution is cooled and filtered and the filtrate is washed with satd. NaHCO3, satd. NaCl, and dried (MgSO4). The solvent is removed under reduced pressure and the crude product (30.6 g) is chromatographed on SilicAR CC-7 (600 g) in hexane. Elution with 20% ethyl acetate/hexane gives 7-(4'-benzyloxybutyl)-7-methyl-1-oxa-cycloheptan-2-one (6) as a clear light yellow oil (24.2 g, 91%): ir (neat) 1720 cm-1 (lactone); nmr (CDCl3) δ1.42 (s, 3H, CH3), 2.64 (m, 2H, OC--CH2 --CH2), 3.50 (m, 2H, O--CH2 --CH2), 4.50 (s, 2H, O--CH2 --Ph), 7.32 (s, 5H, aromatic).

Workup

  1. temperatureis heated
  2. temperatureat reflux under a nitrogen atmosphere for 7 hours
  3. temperatureThe solution is cooled
  4. filtrationfiltered
  5. washthe filtrate is washed with satd
  6. dry with materialNaCl, and dried (MgSO4)
  7. customThe solvent is removed under reduced pressure
  8. customthe crude product (30.6 g) is chromatographed on SilicAR CC-7 (600 g) in hexane
  9. washElution with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-176d9ad8eb594543aea7771fed0d1e9d
Source dataset
uspto-grants-1983_05
Patent number
US04384126

Reaction notes

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