m-Chloroperbenzoic acid → 5-(4-Hydroxybutyl)oxepan-2-one

HRID 1494097Notes

Reaction equation

HRID 1494097 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1.ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][O:12][C:9](=[O:21])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 103297384-(4-Hydroxybutyl)cyclohexanone

Product 1

HCID 103300695-(4-Hydroxybutyl)oxepan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.47 g of 4-(4-hydroxybutyl) cyclohexanone in 80 mL methylene chloride is added 6.81 g of 80-85% m-chloroperbenzoic acid and the mixture is stirred at room temperature for 3 hours. The reaction is quenched by addition of saturated aqueous sodium sulfite solution. The mixture is then poured onto a 10% solution of sodium bicarbonate and the layers are separated. The organic phase is dried, filtered and evaporated to dryness to yield 4-(4-hydroxybutyl)-epsilon-caprolactone as a clear oil.

Workup

  1. customThe reaction is quenched by addition of saturated aqueous sodium sulfite solution
  2. additionThe mixture is then poured onto a 10% solution of sodium bicarbonate
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-8b72aaec744341d39cf7012b545bb407
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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