Sulfuric Acid → alpha-(3,4-Dimethoxy-5-nitrophenyl)-2-thiophenemethanol

HRID 1781921Notes

Reaction equation

HRID 1781921 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[C:15]=1[O:16][CH3:17])[CH:11]=[O:12].[S:21](=O)(=O)(O)O>O1CCCC1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:11]([C:1]2[S:21][CH:4]=[CH:3][CH:2]=2)[OH:12])[CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[C:15]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 108675653,4-Dimethoxy-5-nitrobenzaldehydeHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

18.8 ml of n-butyllithium solution (1.6M in hexane) are added dropwise at -50° within 10 minutes to 4.03 g of thiophone dissolved in 40 ml of tetrahydrofuran. After stirring at -50° for 30 minutes 6.3 g of 3,4-dimethoxy-5-nitrobenzaldehyde dissolved in 100 ml of tetrahydrofuran are added dropwise within 30 minutes. The reaction mixture is stirred at -50° for 1 hour at 0° for 30 minutes and poured into 100 ml of 2N sulphuric acid. The mixture is extracted three times with 100 ml of ether each time; the combined ether phases are washed with sodium chloride solution, dried over sodium sulfate, filtered and evaporated. There is obtained α-(3,4-dimethoxy-5-nitrophenyl)-2-thiophenemethanol of m.p. 79°-81° (from methylene chloride/hexane).

Workup

  1. additionare added dropwise within 30 minutes
  2. extractionThe mixture is extracted three times with 100 ml of ether each time
  3. washthe combined ether phases are washed with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ac475188b08e48ee8e91a622daaf4906
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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