Water → 4-bromophenyl benzoate

HRID 1589495Notes

Reaction equation

HRID 1589495 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(OCC)(=O)C>[C:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 78084-BromophenolHCID 8471Triethylamine

Product 1

HCID 2646614-bromophenyl benzoateYield 86.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 360 g of 4-bromophenol in 4.3 liters of ethyl acetate, was added 326 ml of triethylamine. To the mixture, while being cooled in ice and stirred, was added dropwise 300 g of benzoyl chloride over a period of 90 minutes. After two hours of stirring, water was added to the reaction mixture to remove the triethylamine hydrochloride. The ethyl acetate layer was washed successively with a dilute aqueous alkali solution, dilute hydrochloric acid, and saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and freed from the solvent by distillation. The residue was washed with ethanol and dried to obtain 500 g of 4-bromophenyl benzoate.

Workup

  1. temperatureTo the mixture, while being cooled in ice
  2. stirringAfter two hours of stirring
  3. customto remove the triethylamine hydrochloride
  4. washThe ethyl acetate layer was washed successively with a dilute aqueous alkali solution, dilute hydrochloric acid, and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationfreed from the solvent by distillation
  7. washThe residue was washed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-69466c669f2844d3bd29878aecb1ed03
Source dataset
uspto-grants-1986_02
Patent number
US04570006

Reaction notes

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