m-Chloroperbenzoic acid → HCID 22753324, compound

HRID 2163321Notes

Reaction equation

HRID 2163321 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:11]=3[C:12]=2[C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9](=[O:34])[C:10]3[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:11]=3[C:12]=2[C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9841167Methanone, [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]phenyl-

Product 1

HCID 22753324HCID 22753324, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1.0 gram (3.26 mmoles) of 2-(4-hydroxyphenyl)-3-benzoyl-6-hydroxybenzothiophene in 50 ml. of ethyl acetate was prepared and cooled to 0° C. The mixture was stirred, and 620 mg. (3.59 mmoles) of m-chloroperbenzoic acid were added. The mixture was stirred for one hour and then was allowed to stand overnight under refrigeration. The product was chromatographed rapidly over silica gel in a fritted glass funnel, elution being carried out with a 7:3 mixture of benzene and ethyl acetate followed by pure ethyl acetate to obtain 220 mg. (19 percent) of the title compound. Mass spectrum: Theory, 362; Found, 362.

Workup

  1. stirringThe mixture was stirred for one hour
  2. customThe product was chromatographed rapidly over silica gel in a fritted glass funnel
  3. washelution
  4. additionbeing carried out with a 7:3 mixture of benzene and ethyl acetate
  5. customto obtain 220 mg

Sources & evidence

ORD record
ord-01e1221effd44d519c47d61dfd2746b2
Source dataset
uspto-grants-1979_01
Patent number
US04133814

Reaction notes

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