Dicyclohexylcarbodiimide → HCID 53245019, compound

HRID 1026787Notes

Reaction equation

HRID 1026787 reaction equation
[C:1]([O:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])(=[O:3])[CH3:2].[C:16]1([C:22]([O:24]O)=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)C.ClCCl.C(OCC)C>[C:1]([O:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:11][O:24][C:22](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:10])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 523077Perbenzoic acidHCID 67236283HCID 67236283, compound

Product 1

HCID 53245019HCID 53245019, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

5 g (24 mmol) of 2-acetoxymethoxy-benzoic acid (prepared as described in example 1-2) and 3.3 g (24 mmol) of benzenecarboperoxoic acid are dissolved in 150 mL of diethyl ether/dichloromethane mixture, 6/4. The solution is cooled to 0° C., then 4.9 g (24 mmol) of N,N′-dicyclohexylcarbodiimide dissolved in 85 ml of diethyl ether is added dropwise. After stirring for 3 hours at 0° C., the reaction mixture is filtered and then concentrated. The residue is precipitated in diethyl ether and the filtrate is concentrated under reduced pressure. 5 g of (2-acetoxymethoxy-benzoyl)benzoyl peroxide is obtained in the form of white solid at a yield of 63%.

Workup

  1. additionis added dropwise
  2. filtrationthe reaction mixture is filtered
  3. concentrationconcentrated
  4. customThe residue is precipitated in diethyl ether
  5. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-21377ae6b175424a90da9223e0fb8004
Source dataset
uspto-grants-2014_05
Patent number
US08729312B2

Reaction notes

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