Hydrochloric Acid → 2-Hydroxy-3-(2-nitrophenyl)propanoic acid

HRID 236664Notes

Reaction equation

HRID 236664 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+].Cl>O.C(O)CCCCCCCCC>[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 795833-(2-Nitrophenyl)-2-oxopropanoic acidHCID 4311764Sodium borohydride

Product 1

HCID 136517582-Hydroxy-3-(2-nitrophenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 81741-DecanolCatalystHCID 962WaterSolvent

Procedure

To a magnetically stirred suspension of α-oxo-2-nitrobenzenepropanoic acid (5.00 g) in water (75 ml) containing 1 drop of decyl alcohol was added sodium borohydride (2.50 g) in portions to maintain a temperature between 45° and 50°. The resulting solution was then left at room temperature for 21/2 hours. The solution was acidified with concentrated hydrochloric acid and seeded. Stirring and cooling gave crude product; yield 5.01 g, m.p. 84°-90°. Recrystallization from water gave titled product; yield 2.63 g (52%), m.p. 95°-98° with spectral data as above.

Workup

  1. temperatureto maintain a temperature between 45° and 50°
  2. temperaturecooling
  3. customgave crude product
  4. customRecrystallization from water

Sources & evidence

ORD record
ord-a538c6c8f80644e784a4dc9604590fb4
Source dataset
uspto-grants-1987_02
Patent number
US04645857

Reaction notes

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