1-Heptadecene → Oxirane, 2-pentadecyl-

HRID 1906045Notes

Reaction equation

HRID 1906045 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl>[O:26]1[CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:1]1

Participants

4

Reactant 2

HCID 232171-HeptadeceneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 89596Oxirane, 2-pentadecyl-Yield 57.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 100 ml of dichloromethane was dissolved 26.2 g (0.11 mole) of 1-heptadecene, and a solution of 24.5 g of m-chloroperbenzoic acid in 250 ml of dichloromethane was added dropwise to the solution. The mixture was stirred at room temperature overnight. The resulting crystalline precipitate was filtered off and the filtrate was washed with water, aqueous sodium sulfite, aqueous sodium hydrogen carbonate and aqueous sodium chloride, dried and concentrated. The residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (30:1)] to give 16 g of the desired compound as a colorless oil.

Workup

  1. filtrationThe resulting crystalline precipitate was filtered off
  2. washthe filtrate was washed with water, aqueous sodium sulfite, aqueous sodium hydrogen carbonate and aqueous sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (30:1)]

Sources & evidence

ORD record
ord-58b81fd8d72a46648e3f9cd7b6f11494
Source dataset
uspto-grants-1987_03
Patent number
US04649203

Reaction notes

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