1-Octanol → Octyl 2-aminobenzoate

HRID 2397269Notes

Reaction equation

HRID 2397269 reaction equation
C[O-].[Na+].[C:4]([O:13][CH3:14])(=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7].[CH2:15](O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]C>CO>[C:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 8635Methyl AnthranilateHCID 10942334Sodium Methoxide

Product 1

HCID 12590944Octyl 2-aminobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanolic solution of sodium methoxide (prepared from 30 ml of methanol and 0.2 g. of sodium) were added 91 g. of methyl anthranilate and 78 g. of 1-octanol. The reaction mixture was heated at 90° C. for 0.75 hour and at 125° C. for 0.75 hour while methanol was removed by distillation. The residue was washed with water, dried, and distilled. n-Octyl anthranilate was obtained as a clear liquid, b.p. 139°-144° C. at about 0.5 mm.

Workup

  1. customwas removed by distillation
  2. washThe residue was washed with water
  3. customdried
  4. distillationdistilled

Sources & evidence

ORD record
ord-1768970577744967b1bb9b803ddf9550
Source dataset
uspto-grants-1977_05
Patent number
US04021470

Reaction notes

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