Hydrochloric Acid → HCID 21477024, compound

HRID 2293543Notes

Reaction equation

HRID 2293543 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[C:8]([OH:16])[CH:7]=2)[CH2:3][CH2:2]1.[C:17](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.Cl>CC(=O)CC>[CH:1]1([CH2:4][O:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[C:8]([O:16][CH3:17])[CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 21477074HCID 21477074, compound

Product 1

HCID 21477024HCID 21477024, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A 3.00 g portion of methyl 4-cyclopropylmethyloxy-2-hydroxybenzoate was dissolved in 70 ml of 2-butanone, and 2.80 g of potassium carbonate and 1.9 ml of dimethyl sulfate were added, followed by 12 hours of heating under reflux. After completion of the reaction, the solvent was evaporated, the resulting residue was suspended in chloroform, and insoluble matter was removed by celite filtration. The solvent was again evaporated, and then the thus obtained residue was dissolved in 20 ml of tetrahydrofuran, mixed with 30 ml of 2N sodium hydroxide aqueous solution and subjected to 3 hours of heating under reflux. After completion of the reaction, the reaction solution was poured into 1N hydrochloric acid aqueous solution, and the thus precipitated product of interest was collected by filtration, washed with water and then dried under a reduced pressure to give 2.74 g of 4-cyclopropylmethyloxy-2-methoxybenzoic acid.

Workup

  1. temperatureof heating
  2. temperatureunder reflux
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated
  5. custominsoluble matter was removed by celite filtration
  6. customThe solvent was again evaporated
  7. dissolutionthe thus obtained residue was dissolved in 20 ml of tetrahydrofuran
  8. additionmixed with 30 ml of 2N sodium hydroxide aqueous solution
  9. waitsubjected to 3 hours
  10. temperatureof heating
  11. temperatureunder reflux
  12. customAfter completion of the reaction
  13. filtrationthe thus precipitated product of interest was collected by filtration
  14. washwashed with water
  15. customdried under a reduced pressure

Sources & evidence

ORD record
ord-68e449e86aef46128c19a69481184499
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

Loading…