Acetic Acid → 1-(4-Methoxyphenyl)-4-methyl-4-nitro-3-(thiophen-2-yl)pentan-1-one

HRID 904063Notes

Reaction equation

HRID 904063 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[S:6][CH:7]=1.[N+:18]([CH:21]([CH3:23])[CH3:22])([O-:20])=[O:19].C[O-].[Na+].[C:27](O)(=[O:29])C>CO>[CH3:27][O:29][C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[CH2:9][CH:8]([C:5]2[S:6][CH:7]=[CH:3][CH:4]=2)[C:21]([CH3:23])([N+:18]([O-:20])=[O:19])[CH3:22])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3982-NitropropaneHCID 10942334Sodium MethoxideHCID 54514939HCID 54514939, compound

Product 1

HCID 128059131-(4-Methoxyphenyl)-4-methyl-4-nitro-3-(thiophen-2-yl)pentan-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

168 g of 4-methoxy-3-(2-thienyl)-acrylophenone are heated to the boiling point together with 267 g of 2-nitropropane and 400 ml of absolute methanol. A solution of 43 g of sodium methylate in absolute methanol is added within 60 minutes. The resulting mixture is still refluxed during 3 hours. After cooling 43 g of glacial acetic acid are added to the reaction mixture, which is then evaporated to dryness. The residue is taken up with 1500 ml of dichloromethane. This solution is twice washed with 500 ml of water each time, dried over sodium sulfate and evaporated to dryness. The residue crystallises from ethanol and yields 4'-methoxy-4-methyl-4-nitro-3-(2-thienyl)-valerophenone of melting point 90° C.

Workup

  1. temperatureThe resulting mixture is still refluxed during 3 hours
  2. additionare added to the reaction mixture, which
  3. customis then evaporated to dryness
  4. washThis solution is twice washed with 500 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue crystallises from ethanol

Sources & evidence

ORD record
ord-d4192da992ce4dfb8f96a66633dc07ae
Source dataset
uspto-grants-1980_10
Patent number
US04230623

Reaction notes

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