m-Chloroperbenzoic acid → [1-(Hexadecyloxy)ethyl]oxirane

HRID 1761727Notes

Reaction equation

HRID 1761727 reaction equation
[CH3:1][CH:2]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:3]=[CH2:4].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[CH2:6]([O:5][CH:2]([CH:3]1[CH2:4][O:30]1)[CH3:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 145008571-[(1-Methyl-2-propenyl)oxy]hexadecane

Product 1

HCID 14500858[1-(Hexadecyloxy)ethyl]oxirane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 46.9 g of 1-[(1-methyl-2-propenyl)oxy]hexadecane, 32.19 g of m-chloroperbenzoic acid and 300 ml of methylene chloride was stirred overnight and then filtered. The filtrate was evaporated and the residue dissolved in petroleum ether:ether and washed with saturated aqueous sodium bicarbonate. The solution was dried, the solvent removed and the residue chromatographed via HPLC (two columns), eluting first with hexane to remove higher Rf impurities and then with 10% ether in hexane to elute the product, giving the desired compound as a clear oil.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. dissolutionthe residue dissolved in petroleum ether
  4. washether and washed with saturated aqueous sodium bicarbonate
  5. customThe solution was dried
  6. customthe solvent removed
  7. customthe residue chromatographed via HPLC (two columns)
  8. washeluting first with hexane
  9. customto remove higher Rf impurities
  10. washwith 10% ether in hexane to elute the product

Sources & evidence

ORD record
ord-29be474f71ba4b7d847c4811d7c7bfa1
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

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