Benzyl Bromide → HCID 19938101, compound

HRID 36449Notes

Reaction equation

HRID 36449 reaction equation
[CH:1]1[CH:6]=[C:5]([CH:7]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[C:4]([C:22]([OH:24])=[O:23])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(C(C)=O)C>[CH2:31]([O:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:4]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)=[CH:17][CH:16]=2)[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=2[C:22]([O:24][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:23])=[CH:13][CH:12]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66494Phenolphthalin

Product 1

HCID 19938101HCID 19938101, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In 500 ml of methyl ethyl ketone were dissolved 50 g of phenolphthalin and 75 g of anhydrous potassium carbonate, and the solution was ice cooled. Subsequently, 58 ml of benzyl bromide was added dropwise to the solution, and the mixture was heated under reflux for 24 hours. The temperature of the mixture was brought back to room temperature, and concentrated. Thereafter, water was added to the residue, and the aqueous mixture was extracted with ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with an aqueous 10% citric acid and then dried over anhydrous magnesium sulfate. The solvent was evaporated to give 114.61 g of the desired product.

Workup

  1. temperaturecooled
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 24 hours
  4. customwas brought back to room temperature
  5. concentrationconcentrated
  6. additionThereafter, water was added to the residue
  7. extractionthe aqueous mixture was extracted with ethyl acetate
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with ethyl acetate
  10. washwashed with an aqueous 10% citric acid
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated

Sources & evidence

ORD record
ord-565e53e27c4f47138306f1fb81a50a47
Source dataset
uspto-grants-1995_05
Patent number
US05413997

Reaction notes

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