Isobutanol → Isobutyl anthranilate

HRID 2163563Notes

Reaction equation

HRID 2163563 reaction equation
C([O:3][C:4](=O)[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7])C.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([OH:23])[CH:20]([CH3:22])[CH3:21]>>[CH2:19]([O:23][C:4](=[O:3])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7])[CH:20]([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 6560IsobutanolHCID 6877Ethyl 2-aminobenzoateHCID 11430Potassium Carbonate

Product 1

HCID 24515Isobutyl anthranilateYield 96%

Procedure

467 parts of anthranilic acid ethyl ester are heated with 1000 parts of isobutanol and 10 parts of potassium carbonate. The separated ethanol is distilled off over a column, this operation requiring about eight hours. After collecting an intermediate fraction being the mixture of both alcohols, the excess quantity of isobutanol is distilled off, the remaining residual quantity being removed in vacuo. The catalyst is filtered off. There are obtained 556 parts of anthranilic acid isobutyl ester (nD25 1.540; anthranilic acid ethyl ester content according to gas chromatography below 2%). The filtrate maintains its limpid character even at prolonged storage. The yield is 96% of the theory.

Workup

  1. distillationThe separated ethanol is distilled off over a column
  2. customAfter collecting an intermediate fraction
  3. additionthe mixture of both alcohols
  4. distillationthe excess quantity of isobutanol is distilled off
  5. customthe remaining residual quantity being removed in vacuo
  6. filtrationThe catalyst is filtered off

Sources & evidence

ORD record
ord-fcc7b104d3c34acd9631be00b556e135
Source dataset
uspto-grants-1979_01
Patent number
US04135050

Reaction notes

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