2-Methyl-1-heptene → 2-Methyl-2-pentyloxirane

HRID 371333Notes

Reaction equation

HRID 371333 reaction equation
[CH3:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH2:3].ClC1C=CC=C(C(OO)=[O:17])C=1>C(Cl)Cl>[CH3:3][C:2]1([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[O:17][CH2:1]1

Participants

4

Reactant 2

HCID 275192-Methyl-1-hepteneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 5590732-Methyl-2-pentyloxiraneYield 40.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-1-heptene 4 (17 g, 0.15 mol) in methylene chloride (300 mL) at 0° C. was added meta-chloroperbenzoic acid (37 g, 0.18 mol) in portions. The reaction mixture was stirred at 0° C. for 30 minutes, then at room temperature overnight. It was cooled in an ice bath and then filtered. The filtrate was washed with 5% sodium hydroxide, saturated sodium chloride and dried over magnesium sulfate; 7.8 g of 2-methyl-1-heptene oxide 5 was obtained after HPLC purification.

Workup

  1. customat room temperature
  2. customovernight
  3. temperatureIt was cooled in an ice bath
  4. filtrationfiltered
  5. washThe filtrate was washed with 5% sodium hydroxide, saturated sodium chloride
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-a182b5f8d36f41f99244e2fc87cfaf07
Source dataset
uspto-grants-1985_07
Patent number
US04530933

Reaction notes

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