2-Chlorobenzene-1-carboperoxoic acid → 4-[[[3-(4-Acetyl-3-hydroxy-2-propylphenoxy]propyl]sulfinyl]methyl]-1,3-oxathiolane-2,2-dipropanoic acid

HRID 1650258Notes

Reaction equation

HRID 1650258 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][CH:14]2[CH2:18][O:17][C:16]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[S:15]2)=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].ClC1C(C(OO)=[O:43])=CC=CC=1>C(Cl)Cl>[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH2:13][CH:14]2[CH2:18][O:17][C:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[S:15]2)=[O:43])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 125873982-Chlorobenzene-1-carboperoxoic acidHCID 144058884-[[[3-(4-Acetyl-3 hydroxy-2-propylphenoxy)propyl]thio]methyl]1,3 oxathiolane-2,2-dipropanoic acid

Product 1

HCID 144059424-[[[3-(4-Acetyl-3-hydroxy-2-propylphenoxy]propyl]sulfinyl]methyl]-1,3-oxathiolane-2,2-dipropanoic acidYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure of Example 46 using the sulfide obtained in Example 3 (0.15 g, 0.0003 mol) and m chloroperbenzoic acid (0.062 g, 0.0003 mol) in methylene chloride (3 ml). The crude product was chromatographed on silica gel using ethyl acetate containing 0.5% acetic acid to give 0.070 g (45%) of the desired product as an oil.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-dad60332ddb54091be55320deaebf916
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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