Potassium Hydroxide → HCID 19386786, compound

HRID 2399269Notes

Reaction equation

HRID 2399269 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:14]([NH2:21])=[CH:15][C:16]=1[O:17][CH2:18][CH:19]=[CH2:20])[C:8]([O:10]CC=C)=[O:9])[CH:2]=[CH2:3].[OH-].[K+]>C(O)C.O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:14]([NH2:21])=[CH:15][C:16]=1[O:17][CH2:18][CH:19]=[CH2:20])[C:8]([OH:10])=[O:9])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19386782HCID 19386782, compound

Product 1

HCID 19386786HCID 19386786, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of allyl 3,4-diallyloxy-6-aminobenzoate * (16 mmol) in ethanol (50 ml) was added a solution of potassium hyroxide (48 mmol) in water (2ml). The mixture was heated at reflux for 40 minutes. The solution was partially evaporated at reduced pressure, acidified with acetic acid and extracted with ethylaceate. The organic layer was washed with water, a saturated solution of sodium chloride, dried (MgSO4) and decolourised with charcoal. Evaporation of the solvent gave 3,4-diallyloxy-6-aminobenzoic acid as a sandy solid. NMR (DMSO-d6): 4.5(m,4H); 5.33 ,4H); 6.60(s,1H); 7.3(s,1H): M/S +ve FAB (M+H)hu +=250.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 40 minutes
  3. customThe solution was partially evaporated at reduced pressure
  4. extractionextracted with ethylaceate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated solution of sodium chloride, dried (MgSO4)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4536d2de4f954304810ff3e8363e20d2
Source dataset
uspto-grants-1995_09
Patent number
US05447925

Reaction notes

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