HCID 86639744, compound → HCID 86639745, compound

HRID 1643234Notes

Reaction equation

HRID 1643234 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:16][C:17]([S:24][C:25]2[CH:30]=[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:28]([OH:35])=[C:27]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:26]=2)([CH3:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>CCCCCC.ClCCl.[O-2].[O-2].[Mn+4]>[C:20]([CH2:19][CH2:18][C:17]1([CH3:23])[S:24][C:25]2([CH:26]=[C:27]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:28](=[O:35])[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:30]2)[C:7]2([CH:8]=[C:9]([C:12]([CH3:14])([CH3:13])[CH3:15])[C:10](=[O:11])[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6]2)[S:16]1)([OH:22])=[O:21]

Participants

5

Reactant 1

HCID 86639744HCID 86639744, compound

Product 1

HCID 86639745HCID 86639745, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

In a mixture of hexane (10 mL) and dichloromethane (10 mL) was dissolved 4,4-bis(3,5-di-t-butyl-4-hydroxyphenylthio)pentanoic acid (600 mg, 1.04 mmol). Manganese dioxide (600 mg) was added to the resulting solution, and the resulting mixture was stirred overnight. The reaction mixture was filtered by using a celite, and the resulting filtrate was concentrated. The residue obtained by the concentration was purified by a flash column chromatography (filler: manufactured by Kanto Kagaku, K.K., 60Nmesh40-100, developing solvent:n-hexane/ethyl acetate (volume ratio)=1/0 to 2/1) to give an objective compound (yield 355 mg and 59%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe resulting filtrate was concentrated
  3. customThe residue obtained by the concentration
  4. customwas purified by a flash column chromatography (filler: manufactured by Kanto Kagaku, K.K., 60Nmesh40-100, developing solvent:n-hexane/ethyl acetate (volume ratio)=1/0 to 2/1)
  5. customto give an objective compound (yield 355 mg and 59%)

Sources & evidence

ORD record
ord-b5d61b38fcf94192a9b52cd975236d38
Source dataset
uspto-grants-2012_02
Patent number
US08119686B2

Reaction notes

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