m-Chloroperbenzoic acid → 3,3-dimethyl-1,4-dioxane-2,5-dione

HRID 1785528Notes

Reaction equation

HRID 1785528 reaction equation
ClC1C=C[CH:5]=[C:4]([C:8]([O:10]O)=[O:9])[CH:3]=1>ClCCl>[CH3:5][C:4]1([CH3:3])[C:8](=[O:9])[O:10][CH2:4][C:8](=[O:9])[O:10]1

Participants

3

Reactant 1

HCID 70297m-Chloroperbenzoic acid

Product 1

HCID 102360123,3-dimethyl-1,4-dioxane-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-18 °C

Procedure

A solution of 5 g of cyclic keto-ester (39 mmol) and 8.1 g of metachloroperbenzoic acid (1.2 eq.) in 40 ml of dichloromethane is heated under reflux for 24 hours. The complete conversion of the ring with 5 members is monitored by NMR 1H on a sample. The reaction medium is then cooled down to −18° C. overnight then filtered on frit in order to eliminate the metachlorobenzoic acid formed. The filtrate is concentrated under vacuum. The residue is recrystallized from ethyl acetate at −18° C. 3.9 g of analytically pure, 3,3-dimethyl-2,5-dioxane-1,4-dione are thus obtained (70% of isolated product yield). The product is characterized by NMR 1H [4.97 (s, 2H), 1.70 (s, 6H)] and 13C [167.7 and 163.9 (C═O), 79.8 (Cq), 65.8 (CH2), 25.8 (CH3)], RX (cf. FIG. 1), mp (84-85° C.) and elementary analysis. Calculated C: 50.00, H: 5.56. Found C: 49.98, H: 5.33.

Workup

  1. temperatureunder reflux for 24 hours
  2. filtrationthen filtered on frit in order
  3. customformed
  4. concentrationThe filtrate is concentrated under vacuum
  5. customThe residue is recrystallized from ethyl acetate at −18° C

Sources & evidence

ORD record
ord-8c87d20b662440d4a55bb0bd3cc07d10
Source dataset
uspto-grants-2009_03
Patent number
US07504524B2

Reaction notes

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