1-Butanol → Butyl anthranilate

HRID 2163565Notes

Reaction equation

HRID 2163565 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[NH2:6].[CH2:12](O)[CH2:13][CH2:14]C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([O:2][C:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[NH2:6])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 8635Methyl AnthranilateHCID 11430Potassium Carbonate

Product 1

HCID 24433Butyl anthranilateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

453 parts of anthranilic acid methyl ester, 444 parts of n-butanol and 11 parts of potassium carbonate are heated together, the methanol thus formed is distilled off over a column. After an intermediate fraction containing methanol and n-butanol, the excess quantity of n-butanol is distilled off, towards the end this latter operational step is carried out in vacuo. The reaction lasts for about nine hours. The residue is distilled in vacuo, there are obtained 556 parts of pure anthranilic acid n-butyl ester (boiling point 130°-140° C. under 7 mm Hg, nD25 1.544, purity according to gas chromatography 99-100%). Yield: 96% of the theory.

Workup

  1. distillationis distilled off over a column
  2. additionAfter an intermediate fraction containing methanol and n-butanol
  3. distillationthe excess quantity of n-butanol is distilled off, towards the end this latter operational step
  4. distillationThe residue is distilled in vacuo, there

Sources & evidence

ORD record
ord-86866861800b4d70bc0dcab20d7a29e9
Source dataset
uspto-grants-1979_01
Patent number
US04135050

Reaction notes

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