4-Hydroxybenzoic Acid → HCID 683761, compound

HRID 1493809Notes

Reaction equation

HRID 1493809 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=C=O)=[CH:15][CH:14]=1.O>[O-]CC.[Na+].CC(N(C)C)=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 1354-Hydroxybenzoic Acid2×HCID 962WaterHCID 794431-Isocyanato-4-methoxybenzene

Product 1

HCID 683761HCID 683761, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 2723922Sodium ethoxideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
30 °C

Procedure

p-Hydroxybenzoic acid (69.06 grams, 0.50 mole), sodium ethoxide catalyst (0.155 gram, 0.225% wt. of the p-hydroxybenzoic acid used) and dimethylacetamide solvent (400 grams) are added to a reactor equipped with a reflux condenser and stirred under a nitrogen atmosphere at 80° C. p-Methoxyphenylisocyanate (78.30 grams, 0.525 mole) is added dropwise over a ten minute period with cooling of the reactor exterior to maintain the 80° C. reaction temperature. After an additional ten minutes at 80620 C., heating of the reactor commenced and a 160° C. temperature is achieved 25 minutes later. After three hours at the 160° C. reaction temperature, the reactor is cooled to 30° C. then the contents poured into two liters of deionized water. A precipitated white powder is recovered via filtration of the aqueous slurry then dissolved into one liter of boiling methanol. After cooling the methanol solution to 5° C., a first crop of white crystalline product is filtered off and dried at 90° C. under vacuum to a constant weight of 67.9 grams. The methanol solution is concentrated by rotary evaporation to a 300 milliliter volume then cooled to 5° C. until a second crop of white crystalline product appeared. After filtration, drying of the product to constant weight provided an additional 30.8 grams to give a total isolated yield of 81.2% of 4-hydroxy-4'-methoxybenzanilide.

Workup

  1. additionare added to a reactor
  2. customequipped with a reflux condenser
  3. additionis added dropwise over a ten minute period
  4. temperaturewith cooling of the reactor exterior
  5. temperatureto maintain
  6. customthe 80° C. reaction temperature
  7. waitAfter an additional ten minutes at 80620 C
  8. temperature, heating of the reactor
  9. customcommenced and a 160° C.
  10. customAfter three hours at the 160° C. reaction temperature
  11. filtrationA precipitated white powder is recovered via filtration of the aqueous slurry
  12. dissolutionthen dissolved into one liter of boiling methanol
  13. temperatureAfter cooling the methanol solution to 5° C.
  14. filtrationa first crop of white crystalline product is filtered off
  15. customdried at 90° C. under vacuum to a constant weight of 67.9 grams
  16. concentrationThe methanol solution is concentrated by rotary evaporation to a 300 milliliter volume
  17. temperaturethen cooled to 5° C. until a second crop of white crystalline product
  18. filtrationAfter filtration
  19. customdrying of the product to constant weight
  20. customprovided an additional 30.8 grams
  21. customto give

Sources & evidence

ORD record
ord-a260ec844dcd4794a7fed672a1190735
Source dataset
uspto-grants-1991_06
Patent number
US05024785

Reaction notes

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