Hydrochloric Acid → Ethyl 2-(4-bromophenethyl)-benzoate

HRID 1288542Notes

Reaction equation

HRID 1288542 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.Cl.[CH2:20](O)[CH3:21]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([O:12][CH2:20][CH3:21])=[O:11])=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 11449587Benzoic acid, 2-[2-(4-bromophenyl)ethyl]-

Product 1

HCID 21502882Ethyl 2-(4-bromophenethyl)-benzoate

Procedure

A solution of 40 g. (0.131 mole) of 2-(4-bromophenethyl)-benzoic acid in 250 ml. of absolute ethanol is stirred and heated to refluxing while hydrogen chloride is introduced into the solution for 2 hours. After standing at room temperature for 2 1/2 days, the mixture again is stirred at reflux for 12 hours and, during this period, hydrogen chloride is passed into the solution for 1 hour. The two-phase mixture is evaporated to dryness under reduced pressure and the residue partitioned between benzene and water. The combined benzene layers are extracted with 5% aqueous sodium hydroxide and then washed thoroughly with water and dried over anhydrous sodium sulfate. Evaporation of the solvent and distillation of the residue in vacuo gives the product as the oily distillate, b.p. 142°/0.2 mm.

Workup

  1. temperatureheated
  2. additionis introduced into the solution for 2 hours
  3. customAfter standing at room temperature for 2 1/2 days
  4. temperatureat reflux for 12 hours and, during this period
  5. customThe two-phase mixture is evaporated to dryness under reduced pressure
  6. customthe residue partitioned between benzene and water
  7. extractionThe combined benzene layers are extracted with 5% aqueous sodium hydroxide
  8. washwashed thoroughly with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customEvaporation of the solvent and distillation of the residue in vacuo
  11. customgives the product as the oily distillate, b.p. 142°/0.2 mm

Sources & evidence

ORD record
ord-8f8bd9b22b3e49f38932142e4f06f725
Source dataset
uspto-grants-1976_10
Patent number
US03988454

Reaction notes

Loading…