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Bismuth-oxygen → 1-(3-Methylphenyl)-2-[4-(methylthio)phenyl]ethane-1,2-dione

HRID 2231126
Notes
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Reaction equation

HRID 2231126 reaction equation
[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1)=[O:4].[Bi]=O>C(O)(=O)C>[CH3:11][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[C:2]([C:12]2[CH:13]=[CH:14][C:15]([S:18][CH3:19])=[CH:16][CH:17]=2)=[O:1])[CH:10]=[CH:9][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6327914Bismuth-oxygen2×HCID 184638162-Hydroxy-1-(3-methylphenyl)-2-[4-(methylthio)phenyl]-ethanone

Product 1

HCID 184636051-(3-Methylphenyl)-2-[4-(methylthio)phenyl]ethane-1,2-dioneYield 43.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

The ketone from step 2 (30.5 mmol, 8.31 g) was diluted with acetic acid (90 ml) and heated to ˜90° C. Bi2O3 (30.5 mmol, 14.2 g) was added. After stirring 15 minutes, additional bismuth oxide (15 mmol, 7 g) was added. After 30 additional minutes, the mixture was filtered through silica and Celite®, then lyophilized. The residue was subjected to chromatography (3:1 hexane: ethyl acetate), affording the title compound as a yellow solid (3.56 g, 43%), which was used in the next step.

Workup

  1. filtrationAfter 30 additional minutes, the mixture was filtered through silica and Celite®

Sources & evidence

ORD record
ord-9a90ca9d028f4129a8f56a4dc44650dd
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06426360B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes