3-(2-Nitrophenyl)-2-oxopropanoic acid → 2-Hydroxy-3-(2-nitrophenyl)propanoic acid

HRID 1381314Notes

Reaction equation

HRID 1381314 reaction equation
[O:1]=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])[C:3]([OH:5])=[O:4].[BH4-].[Na+]>C(O)C>[OH:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 795833-(2-Nitrophenyl)-2-oxopropanoic acidHCID 4311764Sodium borohydride

Product 1

HCID 136517582-Hydroxy-3-(2-nitrophenyl)propanoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a magnetically stirred solution of α-oxo-2-nitrobenzenepropanoic acid (40.00 g) in absolute ethanol (500 ml) cooled in ice water was added sodium borohydride (20.0 g) in portions at such a rate as to maintain the temperature between 25 and 30°. The temperature of the solution was maintained between 25°-30° for a further 4 hours after the addition. The solution was evaporated to near dryness, and the residue was dissolved in water. The solution was acidified with concentrated hydrochloric acid and extracted four times with ethyl acetate. The organic extract was washed twice with water and dried over magnesium sulfate. Evaporation gave a syrup which was crystallized (seeding) from dichloromethane-cyclohexane; yield 28.26 g (70%), m.p. 87°-90°. Recrystallization with decolorization from water gave 20.31 g. (50%) of the titled compound; m.p. 104°-105°; MH+ 212 (CI mode), λmaxKBr 1715 (COOH), 3445 (OH) cm-1 ; pmr (CDCl3, DMSO-d 6) δ3.04-3.72 (8 lines, AB part of an ABX system, --CH2 --), 4.34-4.54 (q centered at 4.45, width 12 Hz, symmetrically spaced, X part of ABX system, --CH(OH)), 7.28-7.68 (m, 3 aromatic protons and exchangeable OH), 7.80-8.00 ("d" centered at 7.95, "J" 8 Hz, 1 aromatic proton).

Workup

  1. temperatureto maintain the temperature between 25 and 30°
  2. temperatureThe temperature of the solution was maintained between 25°-30° for a further 4 hours
  3. additionafter the addition
  4. customThe solution was evaporated
  5. dissolutionthe residue was dissolved in water
  6. extractionextracted four times with ethyl acetate
  7. extractionThe organic extract
  8. washwas washed twice with water
  9. dry with materialdried over magnesium sulfate
  10. customEvaporation
  11. customgave a syrup which
  12. customwas crystallized (seeding) from dichloromethane-cyclohexane
  13. customRecrystallization with decolorization from water
  14. customgave 20.31 g

Sources & evidence

ORD record
ord-5a4e6316be6e4d0ebb2862d0d2b27cb3
Source dataset
uspto-grants-1986_04
Patent number
US04585879

Reaction notes

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