Benzyl Bromide → HCID 67919656, compound

HRID 893029Notes

Reaction equation

HRID 893029 reaction equation
[OH:1][CH:2]([CH2:11][C:12]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:1][CH:2]([CH2:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67919701HCID 67919701, compound

Product 1

HCID 67919656HCID 67919656, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20.8 g (86 mmole) 2,5-dihydroxy-β-phenylpropiophenone, 15.4 ml (130 mmole) benzyl bromide and 12.5 g (90 mmole) potassium carbonate were heated under reflux for 3 hours with 200 ml acetone. After distilling off the solvent, the residue was dissolved in ethylacetate and extracted three times with 150 ml each of 2N sodium hydroxide solution. Subsequently the organic phase was extracted with 150 ml 2N hydrochloric acid and then washed with water to neutrality. After that, the organic phase was separated, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was recrystallized from ethanol/acetone (2:1).

Workup

  1. distillationAfter distilling off the solvent
  2. dissolutionthe residue was dissolved in ethylacetate
  3. extractionextracted three times with 150 ml each of 2N sodium hydroxide solution
  4. extractionSubsequently the organic phase was extracted with 150 ml 2N hydrochloric acid
  5. washwashed with water to neutrality
  6. customAfter that, the organic phase was separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure
  10. customThe residue was recrystallized from ethanol/acetone (2:1)

Sources & evidence

ORD record
ord-8111fe65fe30432296fa1d6953971de0
Source dataset
uspto-grants-1992_06
Patent number
US05120874

Reaction notes

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