Peracetic Acid → HCID 68485140, compound

HRID 1191587Notes

Reaction equation

HRID 1191587 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[C:11]([CH:17]2[C:22](=[O:23])[C:21]([CH3:25])([CH3:24])[S:20][C:19]([CH3:27])([CH3:26])[C:18]2=[O:28])[CH:10]=1.C(OO)(=[O:31])C>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[C:11]([CH:17]2[C:22](=[O:23])[C:21]([CH3:25])([CH3:24])[S:20](=[O:31])[C:19]([CH3:27])([CH3:26])[C:18]2=[O:28])[CH:10]=1

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 68486440HCID 68486440, compound

Product 1

HCID 68485140HCID 68485140, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylthiopyran-3,5-dione (79 mg, 0.1816 mmol), peracetic acid (1.8 g, 7.2 mmol, 36-40% solution in acetic acid) and dichloromethane (0.23 ml) is stirred for 4 hours at ambient temperature. The reaction mixture is partitioned between water and dichloromethane, and the organic phase is separated then concentrated under reduced pressure. The residue is purified by preparative reverse phase HPLC to give 4-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-1-oxothiopyran-3,5-dione (32.9 mg) as a clear gum.

Workup

  1. customThe reaction mixture is partitioned between water and dichloromethane
  2. customthe organic phase is separated
  3. concentrationthen concentrated under reduced pressure
  4. customThe residue is purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-3f1204e724704b19972d21652f92ea03
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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