p-Toluenesulfonic acid → HCID 15819505, compound

HRID 486909Notes

Reaction equation

HRID 486909 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:7]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:8][C:9]2[O:13][CH2:12][O:11][C:10]=2[CH:14]=1)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>CO.O.C(O)C>[CH3:1][O:4][CH2:5][C:6]1[C:7]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:8][C:9]2[O:13][CH2:12][O:11][C:10]=2[CH:14]=1

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 15819508HCID 15819508, compound

Product 1

HCID 15819505HCID 15819505, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.6 g of 3-(6-acetoxymethyl-1,3-benzodioxole-5-yl)propionic acid was dissolved in 100 ml of methanol. A catalytic amount of p-toluenesulfonic acid was added to the solution and the mixture was heated under reflux for 4 h and 15 min. The solvent was distillef off from the reaction mixture. A solution of 1 g of sodium hydroxide in a mixture of 5 ml of water and 45 ml of ethanol was added to the residue and the mixture was heated under reflux for 20 min. The reaction mixture was concentrated. 200 ml of ethyl acetate and 200 ml of water were added to the concentrate. The mixture was acidified with concentrated hydrochloric acid. The layers thus formed were separated. The product was washed with water three times and then dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 1.25 g of the intended compound in the form of a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 h and 15 min
  3. additionwas added to the residue
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 20 min
  6. concentrationThe reaction mixture was concentrated
  7. addition200 ml of ethyl acetate and 200 ml of water were added to the concentrate
  8. customThe layers thus formed
  9. customwere separated
  10. washThe product was washed with water three times
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-73f209e57b6e462cbb05c4fda4384d33
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

Loading…