2-Chlorobenzene-1-carboperoxoic acid → HCID 53778012, compound

HRID 1740280Notes

Reaction equation

HRID 1740280 reaction equation
ClC1C(C(OO)=[O:9])=CC=CC=1.[CH2:12]([O:14][C:15](=[O:37])[C:16]([Cl:36])([Cl:35])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[CH3:13]>ClCCl>[CH2:12]([O:14][C:15](=[O:37])[C:16]([Cl:36])([Cl:35])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:27]([C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)=[O:9])[CH3:13]

Participants

4

Reactant 2

HCID 125873982-Chlorobenzene-1-carboperoxoic acidHCID 537675782,2-Dichloro-12-(4-chlorophenylsulfenyl)-dodecanoic acid ethyl ester

Product 1

HCID 53778012HCID 53778012, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.59 g (3.41 mmol) chloroperbenzoic acid dissolved in 15 ml dichloromethane was added dropwise to a solution of 1.5 g (3.41 mmol) 104 in 30 ml dichloromethane analogously to example 25 (preparation of 77). 1.24 g (80%) 105 was obtained after flash chromatography on silica gel. 1.24 g (2.72 mmol) 105 was admixed with 5.5 ml ethanol and 5.5 ml 1 N KOH and cooled for 5 hours at room temperature. It was cooled to 0° C. and acidified with 2 N HCl. The precipitated precipitate was suction filtered, washed with water and isohexane and dried in a vacuum, yield: 0.65 g (56%) 55. The sodium salt prepared from 55 and pulverized NaOH in ethanol melted at 91-94° C.

Sources & evidence

ORD record
ord-ca556f0f7e5e46c8a4900aeb360589a3
Source dataset
uspto-grants-1999_10
Patent number
US05968982

Reaction notes

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