m-Chloroperbenzoic acid → 9,10-Epoxy-6,9,10-trimethyl-undec-5-en-2-one

HRID 1657573Notes

Reaction equation

HRID 1657573 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][C:11]([CH3:15])=[C:12]([CH3:14])[CH3:13])=[CH:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[O:24]1[C:12]([CH3:14])([CH3:13])[C:11]1([CH3:15])[CH2:10][CH2:9][C:2]([CH3:1])=[CH:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 545072266,9,10-Trimethyl-undeca-5,9-dien-2-one

Product 1

HCID 541284819,10-Epoxy-6,9,10-trimethyl-undec-5-en-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 100 g. of 6,9,10-trimethyl-undeca-5,9-dien-2-one in 2,000 ml. of methylene chloride, there was added while cooling with ice, 100 g. of m-chloroperbenzoic acid. The resulting mixture was allowed to stand while constantly stirring at room temperature for 1 hour. The resulting mixture was diluted with 1,000 ml. of methylene chloride. The resulting solution was washed with ice-cold 1N sodium hydroxide solution and with a saturated sodium chloride solution, dried over sodium sulfate and evaporated. The residue was fractionally distilled under high vacuum. There was obtained 9,10-epoxy-6,9,10-trimethyl-undec-5-en-2-one; b.p. 89°-91°C./0.07 mmHg; nD20 = 1.4656.

Workup

  1. temperaturewhile cooling with ice, 100 g
  2. additionThe resulting mixture was diluted with 1,000 ml
  3. washThe resulting solution was washed with ice-cold 1N sodium hydroxide solution and with a saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. distillationThe residue was fractionally distilled under high vacuum

Sources & evidence

ORD record
ord-e8e6f4c691f041b8a0c225ba87208cab
Source dataset
uspto-grants-1976_06
Patent number
US03961051

Reaction notes

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