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

HRID 274440Notes

Reaction equation

HRID 274440 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 chromato graphed 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

Sources & evidence

ORD record
ord-7f705cc59c854636ad254ff1b942e9c2
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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