Benzaldehyde → Benzoic acid, 2-hydroxy-5-[(phenylmethylene)amino]-

HRID 2107005Notes

Reaction equation

HRID 2107005 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 40755-Aminosalicylic Acid

Product 1

HCID 793576Benzoic acid, 2-hydroxy-5-[(phenylmethylene)amino]-Yield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Hydroxy-5-aminobenzoic acid (10.0 g, 65 mmole) was mixed with benzaldehyde (30 ml) and heated to boiling until a clear solution was obtained. To the solution ice-cooled toluene (100 ml) was added, the precipitated crystals filtered off and washed with cold absolute ethanol (2×25 ml) followed by petroleum ether (3×25 ml) and dried, in vacuo, to give the title compound (6.8 g, 47%), m.p. 213°-215° C. Found (Calc. for C14H11NO3) C 69.28 (69.70), H 4.73 (4.56), N 5.73 (5.81).

Workup

  1. temperatureheated
  2. customwas obtained
  3. additionwas added
  4. filtrationthe precipitated crystals filtered off
  5. washwashed with cold absolute ethanol (2×25 ml)
  6. customdried, in vacuo

Sources & evidence

ORD record
ord-10b83e6b1ff44164937903e8e142ce95
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Reaction notes

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