Water → HCID 15383033, compound

HRID 850398Notes

Reaction equation

HRID 850398 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+].[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1.O>CC(C)=O>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][O:1][C:2]2[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 15462892HCID 15462892, compound

Product 1

HCID 15383033HCID 15383033, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 4-hydroxy-3-isobutylbenzoate (25.6 g), potassium carbonate (31.8 g), and 4-fluorobenzyl bromide (26.1 g) were refluxed in acetone (150 ml) with stirring for 4 hours. The reaction mixture, with water added thereto, was extracted with ethyl acetate. The extract was concentrated under a vacuum. The resulting residue, with water (50 ml), potassium hydroxide (12.9 g), and ethanol (100 ml) added thereto, was refluxed with stirring for 2 hours. The reaction mixture, with water added thereto, was neutralized with hydrochloric acid and then extracted with ethyl acetate. The extract was washed with 10% hydrochloric acid and water successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. Thus obtained solid was recrystallized from n-hexane/ethanol, thereby yielding 30.8 g of the aimed compound.

Workup

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

Sources & evidence

ORD record
ord-46b8f30a980e46fbbdca79cda1d33133
Source dataset
uspto-grants-2000_01
Patent number
US06017937

Reaction notes

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