m-Chloroperbenzoic acid → HCID 57595931, compound

HRID 1785530Notes

Reaction equation

HRID 1785530 reaction equation
ClC1C=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=[O:9])[CH:3]=1>ClCCl>[CH2:5]([C:4]1([CH3:3])[C:8](=[O:9])[O:10][CH2:4][C:8](=[O:9])[O:10]1)[CH3:6]

Participants

3

Reactant 1

HCID 70297m-Chloroperbenzoic acid

Product 1

HCID 57595931HCID 57595931, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.5 g of cyclic keto-ester (3.5 mmol) and 1.21 g of metachloroperbenzoic acid (2 eq.) in 10 ml of dichloromethane is heated under reflux for 48 hours. After returning to ambient temperature, the solvent is eliminated under vacuum. NMR 1H analysis reveals the complete conversion of the ring with 5 members and the formation of mostly 3-ethyl-3-methyl-2,5-dioxane-1,4-dione (spectroscopic yield: 75%). NMR 1H characteristics [4.97 (s, 2H), 1.95 (q, 2H, 3JHH=7.5 Hz), 1.67 (s, 3H), 1.03 (t, 3H, 3JHH=7.5 Hz)].

Workup

  1. temperatureunder reflux for 48 hours
  2. customAfter returning to ambient temperature

Sources & evidence

ORD record
ord-19d94f0f1bb1409e909c25ac1d6bf545
Source dataset
uspto-grants-2009_03
Patent number
US07504524B2

Reaction notes

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