4-Nitrophenylglyoxylic acid → 1-(4-nitrophenyl)ethane-1,2-diol

HRID 977067Notes

Reaction equation

HRID 977067 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:14])[C:11](O)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:14])[CH2:11][OH:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 1519404-Nitrophenylglyoxylic acid

Product 1

HCID 41172001-(4-nitrophenyl)ethane-1,2-diolYield 119.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7 ml of a 1.0M tetrahydrofuran solution of diborane-tetrahydrofuran complex were added, at 0° C. under a stream of nitrogen, to a solution of 0.5 g of crude 4-nitrophenylglyoxylic acid in tetrahydrofuran, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off, to give 0.56 g (quantitative yield) of 1-(4-nitrophenyl)-1,2-ethanediol as a crude product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-c4ba663b7fc3459fa40360bb99dc689d
Source dataset
uspto-grants-1997_03
Patent number
US05614470

Reaction notes

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