m-Chloroperbenzoic acid → Ethyl 6-(benzenesulphinylmethyl)-3-ethyl-2-methoxybenzoate

HRID 2177688Notes

Reaction equation

HRID 2177688 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([S:18][CH2:19][C:20]2[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([O:31][CH3:32])[C:23]([CH2:33][CH3:34])=[CH:22][CH:21]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[C:12]1([S:18]([CH2:19][C:20]2[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([O:31][CH3:32])[C:23]([CH2:33][CH3:34])=[CH:22][CH:21]=2)=[O:9])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67107436Ethyl 6-(phenylthiomethyl)-3-ethyl-2-methoxybenzoate2×

Product 1

HCID 67107367Ethyl 6-(benzenesulphinylmethyl)-3-ethyl-2-methoxybenzoateYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (0.07 g) was added to a stirred solution of ethyl 6-(phenylthiomethyl)-3-ethyl-2-methoxybenzoate (Intermediate 19, 0.315 g) in DCM (5 ml) and the resultant mixture was stirred at room temperature overnight. The solution was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give ethyl 6-(benzenesulphinylmethyl)-3-ethyl-2-methoxybenzoate (0.095 g) as a clear gum.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue was purified by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

Sources & evidence

ORD record
ord-b4d7d2ca37ba4c18afb332c68cc5581a
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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