Water → HCID 15462893, compound

HRID 1292096Notes

Reaction equation

HRID 1292096 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, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 4-hydroxy-3-isobutylbenzoate (25.6 g), potassium carbonate (31.8 g), and benzyl bromide (23.6 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) so as to yield 29.0 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) so as

Sources & evidence

ORD record
ord-de879df073774acfb92ae38e460ec7dd
Source dataset
uspto-grants-1998_05
Patent number
US05756505

Reaction notes

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