Hydrochloric Acid → 4-Geranyloxybenzoic acid

HRID 611702Notes

Reaction equation

HRID 611702 reaction equation
[CH2:1]([O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[OH-].[K+].Cl>CO>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14457497HCID 14457497, compound

Product 1

HCID 123615004-Geranyloxybenzoic acidYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-geranyloxybenzoate(13.00 g) in methanol(50 ml) was added aqueous solution(10 ml) of potassium hydroxide (3.90 g). After being stirred overnight at room temperature, the mixture was refluxed with heating for 1 hour. After being acidified with concentrated hydrochloric acid, the reaction mixture was extracted with chloroform. The organic layer was dried over sodium sulfate anhydride and then the solvent was evaporated out under a vacuum. The resulting solid was recrystallized from hexane/ethyl acetate mixed solution, thereby yielding 9.77 g(71%) of the aimed compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 1 hour
  3. extractionthe reaction mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate anhydride
  5. customthe solvent was evaporated out under a vacuum
  6. customThe resulting solid was recrystallized from hexane/ethyl acetate mixed solution

Sources & evidence

ORD record
ord-cce2d03b550b4637a34391a669b46236
Source dataset
uspto-grants-1999_12
Patent number
US06001880

Reaction notes

Loading…