Sulfuric Acid → 3,4-Dimethoxy-5-nitrobenzhydrol

HRID 2260207Notes

Reaction equation

HRID 2260207 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[C:17]=1[O:18][CH3:19])[CH:13]=[O:14].S(=O)(=O)(O)O>O1CCCC1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[C:17]=1[O:18][CH3:19])[CH:13]([OH:14])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 108675653,4-Dimethoxy-5-nitrobenzaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 214589923,4-Dimethoxy-5-nitrobenzhydrol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25 ml of 2M phenyl lithium solution (in benzene/ether (7:3)) are added dropwise within 15 minutes to 10.0 g of 3,4-dimethoxy-5-nitrobenzaldehyde dissolved in 150 ml of tetrahydrofuran and the mixture is stirred at 0° for 1 hour and at 20° for 2 hours. The mixture is subsequently treated with 150 ml of 2N sulfuric acid and extracted three times with 150 ml of ether. The combined ether phases are washed with sodium chloride solution, dried over sodium sulfate and evaporated. The thus-obtained residue is chromatographed on 180 g of silica gel with methylene chloride. There is obtained 3,4-dimethoxy-5-nitrobenzhydrol as an amorphous solid.

Workup

  1. extractionextracted three times with 150 ml of ether
  2. washThe combined ether phases are washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe thus-obtained residue is chromatographed on 180 g of silica gel with methylene chloride

Sources & evidence

ORD record
ord-e2b9618d0bca4e7a900618e5600c2126
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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