m-Chloroperbenzoic acid → HCID 53850092, compound

HRID 2225763Notes

Reaction equation

HRID 2225763 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)=[O:12])=[CH:7][CH:6]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>ClCCl>[CH3:1][O:2][C:3](=[O:27])[C:4](=[O:26])[C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)(=[O:36])=[O:12])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53828882HCID 53828882, compound

Product 1

HCID 53850092HCID 53850092, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of rac.-4-[[2-(2-naphthalenyloxy)ethyl]sulfinyl]-alpha-oxobenzeneacetic acid methyl ester (1 g) in dichloromethane (50 mL) was treated with 85% metachloroperbenzoic acid (0.81 g) and stirred at room temperature for one hour. The mixture was washed with saturated sodium bicarbonate solution, dried (Na2SO4), filtered, passed through silica gel (5 g) and the product eluted with dichloromethane. Crysallization from dichloromethane-hexane gave 0.61 g of 4-[[2-(2-naphthalenyloxy)ethyl]sulfonyl]-alpha-oxobenzeneacetic acid methyl ester, mp 110°-111° C.

Workup

  1. washThe mixture was washed with saturated sodium bicarbonate solution
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. washthe product eluted with dichloromethane

Sources & evidence

ORD record
ord-b910391e6e6643788bb4f08a22746b1c
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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