Benzene → Ethyl 2-(4-bromophenoxy)benzoate

HRID 2412389Notes

Reaction equation

HRID 2412389 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH:18]1C=CC=C[CH:19]=1>C(O)C.S(=O)(=O)(O)O>[CH2:18]([O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=1[O:6][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:17][CH:16]=1)[CH3:19]

Participants

5

Reactant 2

HCID 241BenzeneHCID 19803169HCID 19803169, compound

Product 1

HCID 23464800Ethyl 2-(4-bromophenoxy)benzoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 560.0 g of 2-(4-bromophenoxy)benzoic acid in 1940 ml of absolute benzene, 218 ml of absolute ethanol and 32.6 ml of concentrated sulphuric acid is boiled under reflux for 32 hours, the water that forms being removed in a water separator. The reaction mixture is cooled to 10° and, with the addition of ice, is washed with 1000 ml of water, 500 ml of a 2N aqueous sodium carbonate solution and then once more with 1000 ml of water. The organic phase is separated off, dried over magnesium sulphate and concentrated by evaporation at 40° at a pressure of 11 mm Hg. The residue is distilled in a high vacuum and yields the 2-(4-bromophenoxy)benzoic acid ethyl ester. Boiling point 140°-150°/0.05 mm Hg.

Workup

  1. temperatureunder reflux for 32 hours
  2. customthe water that forms being removed in a water separator
  3. temperatureThe reaction mixture is cooled to 10° and, with the addition of ice
  4. washis washed with 1000 ml of water, 500 ml of a 2N aqueous sodium carbonate solution
  5. customThe organic phase is separated off
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated by evaporation at 40° at a pressure of 11 mm Hg
  8. distillationThe residue is distilled in a high vacuum

Sources & evidence

ORD record
ord-f38a308ee76d4700a228da6169edac94
Source dataset
uspto-grants-1985_01
Patent number
US04492691

Reaction notes

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