Benzene → 1,2-Epoxy-3-tridecanol

HRID 1120

Reaction equation

HRID 1120 reaction equation
[CH2:1]=[CH:2][CH:3]([OH:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].ClC1C=CC=C(C(OO)=[O:23])C=1.C1C=CC=CC=1>CCCCCC>[O:23]1[CH:2]([CH:3]([OH:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:1]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 70297m-Chloroperbenzoic acidHCID 185797Tridec-1-en-3-ol

Product 1

HCID 134206171,2-Epoxy-3-tridecanolYield 74%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 500-ml flask equipped with a stirrer was charged with 23.8 g (0.12 mol) of 1-tridecen-3-ol, 25.0 g (0.145 mol) of m-chloroperbenzoic acid and 250 ml of benzene, and the contents were stirred at room temperature for 48 hours. After completion of the reaction, 200 ml of hexane. Solids deposited were separated by filtration, and the solvent was distilled off under reduced pressure. The resultant residue was purified by column chromatography on silica gel, thereby obtaining 19.0 g (yield: 74%) of 1,2-epoxy-3-tridecanol.

Workup

  1. customA 500-ml flask equipped with a stirrer
  2. customSolids deposited were separated by filtration
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resultant residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-336388df5b80425486bbf74ea75cd7c9
Source dataset
uspto-grants-1998_03
Patent number
US05723497

Linked notes

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