alpha-(3,4-Dimethoxy-5-nitrophenyl)-2-thiophenemethanol → 3,4-Dimethoxy-5-nitrophenyl 2-thienyl ketone

HRID 274563Notes

Reaction equation

HRID 274563 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[OH:15])[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10]>CC(C)=O.[O-2].[O-2].[Mn+4]>[S:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:14]([C:5]1[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:15]

Participants

4

Reactant 1

HCID 21458951alpha-(3,4-Dimethoxy-5-nitrophenyl)-2-thiophenemethanol

Product 1

HCID 179776943,4-Dimethoxy-5-nitrophenyl 2-thienyl ketone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

9.9 g of α-(3,4-dimethoxy-5-nitrophenyl)-2-thiophenemethanol dissolved in 300 ml of acetone are treated with 90 g of manganese dioxide and heated under reflux for 4 hours. The manganese dioxide is removed by suction filtration and the filtrate is evaporated. There is obtained 3,4-dimethoxy-5-nitrophenyl 2-thienyl ketone of m.p. 102°-104° (from methylene chloride/hexane).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customThe manganese dioxide is removed by suction filtration
  4. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-e43290f302cc4971ba54ee9b80d84760
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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