Potassium Hydroxide → 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid

HRID 264358Notes

Reaction equation

HRID 264358 reaction equation
[CH3:1]/[C:2](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:3]\[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[C:8]([OH:16])[CH:7]=1.[OH-].[K+]>CO>[CH3:1]/[C:2](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:3]\[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[C:8]([OH:16])[CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69130305methyl 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoate

Product 1

HCID 104243134-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acidYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol was dissolved 18.1 g (59.5 mmol) of methyl 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoate, and 30 ml of an aqueous solution of 8.35 g (148 mmol) of potassium hydroxide was added thereto, followed by heating under reflux for 5 hours. Methanol was evaporated, and a 12% hydrochloric acid aqueous solution added to the residue, followed by extraction with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous solution of sodium chloride and dried over sodium sulfate, followed by concentration. The resulting crude product was recrystallized from an ethyl acetate/hexane mixed solvent to obtain 13.06 g (yield: 75%) of 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid represented by the following structural formula (hereinafter referred to as compound 39) as white crystals. The analytical results are shown below. ##STR60##

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for 5 hours
  4. customMethanol was evaporated
  5. additiona 12% hydrochloric acid aqueous solution added to the residue
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed successively with water
  8. dry with materiala saturated aqueous solution of sodium chloride and dried over sodium sulfate
  9. concentrationfollowed by concentration
  10. customThe resulting crude product was recrystallized from an ethyl acetate/hexane mixed solvent

Sources & evidence

ORD record
ord-427455fcf095471b9135db3a6791b8e5
Source dataset
uspto-grants-1997_07
Patent number
US05646184

Reaction notes

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