m-Chloroperbenzoic acid → HCID 15332454, compound

HRID 1720197Notes

Reaction equation

HRID 1720197 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][C:13]([CH2:15][CH:16]([CH3:23])[CH2:17][CH:18]([CH3:22])[CH2:19][CH2:20][CH3:21])=[CH2:14]>C(Cl)Cl>[CH3:14][C:13]1([CH2:15][CH:16]([CH3:23])[CH2:17][CH:18]([CH3:22])[CH2:19][CH2:20][CH3:21])[O:6][CH2:12]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5361182,4,6-Trimethyl-1-nonene

Product 1

HCID 15332454HCID 15332454, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

m-Chloroperoxybenzoic acid (7.31 g, 60% purity, 25.42 mmol) was added to a stirred solution of 2,4,6-trimethyl-1-nonene (5) (3.56 g, 21.19 mmol) in 70 ml of dry methylene chloride in a 250 ml flask in an ice bath. The chilled reaction mixture was stirred for one hour, and then stirred vigorously overnight at room temperature. The reaction mixture was cooled to 10° C. before filtering out a white slurry, which was washed with cooled methylene chloride. The combined filtrates were washed three times with cooled aqueous carbonate, water, and brine and dried over sodium sulfate. Evaporation of the solvent yielded a crude oil which was distilled at 65°-70° C. and 1.5 mm Hg to yield pure 2,4,6-trimethyl-1,2-epoxynonane (6).

Workup

  1. customThe chilled reaction mixture
  2. stirringstirred vigorously overnight at room temperature
  3. filtrationbefore filtering out a white slurry, which
  4. washwas washed with cooled methylene chloride
  5. washThe combined filtrates were washed three times with cooled aqueous carbonate, water, and brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent
  8. customyielded a crude oil which
  9. distillationwas distilled at 65°-70° C.

Sources & evidence

ORD record
ord-114c61ec8b21465f9a5a16764f277e1c
Source dataset
uspto-grants-1996_04
Patent number
US05505951

Reaction notes

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