1-Butanol → Butyl anthranilate

HRID 2163564Notes

Reaction equation

HRID 2163564 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 97%

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 and the methanol thus formed is distilled off over a column. A subsequent intermediate fraction contains both methanol and n-butanol. Finally, the excess quantity of n-butanol is distilled off, preferably in vacuo towards the end of this operational step. The reaction time lasts for about 8 hours. After filtration of the catalyst there are obtained 562 parts of anthranilic acid n-butyl ester (nD25 1.545; accoding to gas chromatography of 99-100% purity). Yield: 97% of the theory.

Workup

  1. distillationis distilled off over a column
  2. distillationFinally, the excess quantity of n-butanol is distilled off, preferably in vacuo towards the end of this operational step
  3. filtrationAfter filtration of the catalyst there

Sources & evidence

ORD record
ord-5ccf7f00daf546d890b19b72c3f6cd71
Source dataset
uspto-grants-1979_01
Patent number
US04135050

Reaction notes

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