m-Chloroperbenzoic acid → HCID 15712405, compound

HRID 704123Notes

Reaction equation

HRID 704123 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([O:22][CH2:23][CH2:24][CH2:25][S:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[C:29]([OH:36])[C:28]=2[CH2:37][CH2:38][CH3:39])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:48])C=1>C(Cl)Cl>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([O:22][CH2:23][CH2:24][CH2:25][S:26]([C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[C:29]([OH:36])[C:28]=2[CH2:37][CH2:38][CH3:39])=[O:48])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15712389Ethyl 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyrate

Product 1

HCID 15712405HCID 15712405, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyrate (1.2 g) in methylene chloride (40 ml) was added m-chloroperbenzoic acid (0.51 g) on ice-water bath and was subjected to stirring at the same temperature for 2 hours. The obtained organic layer was washed twice with a cooled aqueous solution of potassium carbonate, then with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated. The resultant residue was purified through silica-gel column chromatography (eluting with benzene:ethyl acetate=1:1) to give the title compound (0.78 g, 63.2%) as colorless crystal, mp 74-76° C.

Workup

  1. washThe obtained organic layer was washed twice with a cooled aqueous solution of potassium carbonate
  2. dry with materialwith a saturated aqueous solution of sodium chloride, dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe resultant residue was purified through silica-gel column chromatography (eluting with benzene:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-958a39a4150c47c49c683f34c089d216
Source dataset
uspto-grants-1991_01
Patent number
US04985585

Reaction notes

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