m-Chloroperbenzoic acid → HCID 53828882, compound

HRID 2225745Notes

Reaction equation

HRID 2225745 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>ClCCl.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[O:35])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54465876HCID 54465876, compound

Product 1

HCID 53828882HCID 53828882, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-[[2-(2-naphthalenyloxy)ethyl]thio]-alpha-oxobenzeneacetic acid methyl ester (2.56 g) in dichloromethane (75 mL) was chilled in ice and 85 % metachloroperbenzoic acid (1.42 g) was added. The mixture was stirred cold for 1 hour, diluted with saturated sodium bicarbonate solution, and extracted with dichloromethane. The dried (Na2SO4) was filtered, evaporated and the residue was crystallized from dichloromethane-hexane to give 2.2 g of rac.-4-[[2-(2-naphthalenyloxy)ethyl]sulfinyl]-alpha-oxobenzeneacetic acid methyl ester, mp 129°-130° C.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe dried (Na2SO4)
  3. filtrationwas filtered
  4. customevaporated
  5. customthe residue was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-a00b6b5d2b5f4ce7a1f1af0c61d3a02d
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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