m-Chloroperbenzoic acid → 2-[2-(Hexadecyloxy)ethyl]oxirane

HRID 255966Notes

Reaction equation

HRID 255966 reaction equation
[CH2:1]([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])[CH2:2][CH:3]=[CH2:4].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[CH2:6]([O:5][CH2:1][CH2:2][CH:3]1[CH2:4][O:30]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 19866525HCID 19866525, compound

Product 1

HCID 139590722-[2-(Hexadecyloxy)ethyl]oxiraneYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 g of 1-(3-butenyloxy)-hexadecane in 640 ml of methylene chloride was added portionwise 69 g of m-chloroperbenzoic acid. The mixture was stirred under argon for 72 hours and then the solvents were removed. The residue was dissolved in ether and washed with saturated aqueous sodium bicarbonate, dried and evaporated to an oil. This oil was distilled (140°-150° C., 0.05 mm Hg) giving 83.4 g of the desired compound as an oil.

Workup

  1. customthe solvents were removed
  2. dissolutionThe residue was dissolved in ether
  3. washwashed with saturated aqueous sodium bicarbonate
  4. customdried
  5. customevaporated to an oil
  6. distillationThis oil was distilled (140°-150° C., 0.05 mm Hg)

Sources & evidence

ORD record
ord-665097a0da96481c953bfc663eb37a30
Source dataset
uspto-grants-1987_10
Patent number
US04699990

Reaction notes

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