p-Toluenesulfonic acid → HCID 21521437, compound

HRID 918230Notes

Reaction equation

HRID 918230 reaction equation
[C:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]([OH:18])[CH:13]1[O:17][CH2:16][CH2:15][CH2:14]1.[C:19](O)(=[O:22])[CH:20]=[CH2:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:12]([O:18][C:19](=[O:22])[CH2:20][CH2:21][NH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH:13]1[O:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 7360Tetrahydrofurfuryl alcoholHCID 86401-Naphthylamine

Product 1

HCID 21521437HCID 21521437, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A coupling component for the preferred dye of this invention was prepared as follows: A mixture of 30 parts of 1-naphthylamine and 43 parts of tetrahydrofurfuryl alcohol was heated to 80°C. Glacial acrylic acid (16.5 parts) was then added dropwise over a 10 minute period at 80°-85°C. When the addition was complete, the mixture was heated to 90°-95°C. and held at that temperature for 17 hours. The reaction mixture was cooled to 30°C. p-Toluenesulfonic acid (12.5 parts) and toluene (40 parts) were then added and the mixture heated to 85°-95°C. to remove the toluene-water azeotrope. The mixture was cooled to 25°C., washed first with 10% aqueous sodium bicarbonate in order to remove the acidic catalyst, and then with water. The mixture was then heated with steam, distillation of the toluene-water azeotrope commencing at 85°C. The temperature gradually increased during the distillation until at 115°C., almost no distillate was apparent. The mixture was cooled to 85°C. and the lower organic layer was separated to yield 60.5 parts (73% yield) of tetrahydrofurfuryl-3-(1-naphthylamino)propionate having a purity of 76% when analyzed by vapor phase chromatography.

Workup

  1. customA coupling component for the preferred dye of this invention was prepared
  2. additionWhen the addition
  3. temperaturethe mixture was heated to 90°-95°C.
  4. additionwere then added
  5. temperaturethe mixture heated to 85°-95°C.
  6. customto remove the toluene-water azeotrope
  7. temperatureThe mixture was cooled to 25°C.
  8. washwashed first with 10% aqueous sodium bicarbonate in order
  9. customto remove the acidic catalyst
  10. temperatureThe mixture was then heated with steam, distillation of the toluene-water
  11. customazeotrope commencing at 85°C
  12. temperatureThe temperature gradually increased during the distillation until at 115°C.
  13. temperatureThe mixture was cooled to 85°C.
  14. customthe lower organic layer was separated

Sources & evidence

ORD record
ord-d390598e031c44a7bb0cc0c9f1785101
Source dataset
uspto-grants-1976_07
Patent number
US03970617

Reaction notes

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