m-Chloroperbenzoic acid → Acetic acid 5-benzenesulfonyl-2-benzyloxy-phenyl ester

HRID 2221310Notes

Reaction equation

HRID 2221310 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:14](C(=O)C)[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=[C:30](C=CC=1)[C:31]([O:33]O)=[O:32]>C(Cl)(Cl)Cl>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[C:14]([O:33][C:31](=[O:32])[CH3:30])[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 597108891-(5-Benzenesulfonyl-2-benzyloxy-phenyl)-ethanone

Product 1

HCID 59710885Acetic acid 5-benzenesulfonyl-2-benzyloxy-phenyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1-(5-benzenesulfonyl-2-benzyloxy-phenyl)-ethanone (2.16 g; 0.059 mol) and meta-chloroperoxybenzoic acid (3.98 g; 0.018 mol, max. 77%) in chloroform (20 mL) was heated under reflux for 18 hours. After cooling to ambient temperature the mixture was diluted with chloroform, filtered, washed with water and saturated sodium bicarbonate, dried (Na2SO4) and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (hexane-ethyl acetate; 1:1) to give acetic acid 5-benzenesulfonyl-2-benzyloxy-phenyl ester (2.1 g; 93%): M. p. 106.9-111.1° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. filtrationfiltered
  3. washwashed with water and saturated sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography on silica gel (hexane-ethyl acetate; 1:1)

Sources & evidence

ORD record
ord-6495e331575b4118b211307b7bca04a9
Source dataset
uspto-grants-2008_05
Patent number
US07368567B2

Reaction notes

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