Water → HCID 15462893, compound

HRID 2287471Notes

Reaction equation

HRID 2287471 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][C:3]=1[CH2:13][CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CC(C)=O>[CH2:23]([O:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH2:13][CH:14]([CH3:15])[CH3:16])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15462892HCID 15462892, compound

Product 1

HCID 15462893HCID 15462893, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 4-hydroxy-3-isobutylbenzoate (25.6 g), potassium carbonate (31.8 g), and benzyl bromide were refluxed with stirring in acetone (150 ml) for 4 hours. The reaction mixture, with water added thereto, was extracted with ethyl acetate. The extract was concentrated under a vacuum and the residue, after water (50 ml), potassium hydroxide (12.9 g), and ethanol (100 ml) were added thereto, was refluxed with heating for 2 hours. The reaction mixture, after water added thereto, was neutralized with hydrochloric acid and then extracted with ethyl acetate. The extract was washed with 10% hydrochloric acid aqueous solution and water, dried over magnesium sulfate anhydride and then concentrated under a vacuum. The resulting solid was recrystallized from n-hexane/ethanol, thereby yielding 29.0 g of the aimed compound.

Workup

  1. extractionwas extracted with ethyl acetate
  2. concentrationThe extract was concentrated under a vacuum
  3. additionthe residue, after water (50 ml), potassium hydroxide (12.9 g), and ethanol (100 ml) were added
  4. temperaturewas refluxed
  5. temperaturewith heating for 2 hours
  6. additionThe reaction mixture, after water added
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with 10% hydrochloric acid aqueous solution and water
  9. dry with materialdried over magnesium sulfate anhydride
  10. concentrationconcentrated under a vacuum
  11. customThe resulting solid was recrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-7b491072b0cf4ee3814c8b446ccf9074
Source dataset
uspto-grants-2000_07
Patent number
US06083987

Reaction notes

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