Hydrochloric Acid → 4-Geranyloxybenzoic acid

HRID 1458285Notes

Reaction equation

HRID 1458285 reaction equation
[CH2:1]([O:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1C(OC)=O)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[OH-:22].[K+].Cl.[CH3:25][OH:26]>>[CH2:1]([O:11][C:12]1[CH:13]=[CH:18][C:19]([C:25]([OH:26])=[O:22])=[CH:20][CH:21]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 67628891HCID 67628891, compound

Product 1

HCID 123615004-Geranyloxybenzoic acidYield 71%

Procedure

To a solution of methyl geranyloxybenzoate (13.00 g) in methanol (50 ml) was added an aqueous solution (10 ml) of potassium hydroxide (3.90 g), After being stirred at room temperature for one night, the mixture was refluxed with heating for 1 hour. Concentrated hydrochloric acid was added to the reaction solution so as to acidified. Then, the resulting solution was extracted with chloroform. The extract was dried over sodium sulfate anhydride and then the solvent was evaporated under a vacuum. The residue was recrystallized from an n-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. extractionThen, the resulting solution was extracted with chloroform
  4. dry with materialThe extract was dried over sodium sulfate anhydride
  5. customthe solvent was evaporated under a vacuum
  6. customThe residue was recrystallized from an n-hexane/ethyl acetate mixed solution

Sources & evidence

ORD record
ord-d4988a2e425f4dbcaee2229ebea7ca6c
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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