Water → HCID 53244623, compound

HRID 511915Notes

Reaction equation

HRID 511915 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](Cl)=[O:10])=[O:5])[CH3:2].[C:16]1([C:22]([O:24][OH:25])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1.O>C(Cl)(Cl)Cl.ClCCl>[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:25][O:24][C:22](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:10])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 523077Perbenzoic acidHCID 86675009HCID 86675009, compound

Product 1

HCID 53244623HCID 53244623, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-18 °C

Procedure

8.6 g (67 mmol) of 2-(ethoxycarbonyloxy)benzoyl chloride (obtained in Example 1.2) and 10.2 g (44 mmol) of benzenecarboperoxoic acid are dissolved in 43 ml of chloroform. The mixture is cooled to −18° C. and then 2.2 ml (38 mmol) of pyridine in 5 ml of dichloromethane are added dropwise. After stirring at −18° C. for 2 hours, water is added and the mixture is extracted with dichloromethane. The organic phase is dried over magnesium sulphate, filtered and then concentrated. The residue is purified by chromatography on silica gel eluted with a pentane/dichloromethane 5/5 mixture. 11 g of (2-(ethoxycarbonyloxy)benzoyl)benzoyl peroxide are obtained in the form of a beige solid with a yield of 75%.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography on silica gel
  6. washeluted with a pentane/dichloromethane 5/5 mixture

Sources & evidence

ORD record
ord-2df086326bd64c78acdd05ad96490f62
Source dataset
uspto-grants-2015_08
Patent number
US09102607B2

Reaction notes

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