m-Chloroperbenzoic acid → HCID 15007348, compound

HRID 728354Notes

Reaction equation

HRID 728354 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:8]([OH:10])=[O:9])[S:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:16]>ClCCl.CO>[CH3:1][S:2]([C:3]1[CH:4]=[C:5]([C:8]([OH:10])=[O:9])[S:6][CH:7]=1)=[O:16]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13415224HCID 13415224, compound

Product 1

HCID 15007348HCID 15007348, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 2.46 g (14.1 mmoles) of 4-methylthio-2-thiophenecarboxylic acid (prepared as described in Example 28 below) in 150 ml dichloromethane and 10 ml methanol was cooled to icebath temperature. A 120 ml dichloromethane solution of 2.82 g (13.9 mmoles) of m-chloroperoxybenzoic acid (technical grade, 80-85%) was slowly added to the cooled reaction solution. After 1 hour the reaction was essentially complete with a colorless precipitate forming. The precipitate was filtered and dried to give 1.18 g (6.20 mmoles) of desired compound as a colorless solid, m.p. 188°-190° C. The concentrated mother liquor was chromatographed (silica gel) to give an additional 0.83 g (4.36 mmoles) of desired 4-methylsulfinyl-2-thiophenecarboxylic acid, total yield 75% (10.56 mmoles).

Workup

  1. customforming
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-f47a168cd5534533bf4ff4a2af28ff29
Source dataset
uspto-grants-1991_09
Patent number
US05047554

Reaction notes

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