Ethanol → Ethyl [4-(2-Bromoethyl)phenyl]acetate

HRID 1391184Notes

Reaction equation

HRID 1391184 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1.S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:19][CH3:20])=[O:12])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 20386065[4-(2-Bromoethyl)phenyl]acetic acid

Product 1

HCID 54408832Ethyl [4-(2-Bromoethyl)phenyl]acetate

Procedure

A solution of [4-(2-bromoethyl)phenyl]acetic acid (48.6 g., 0.2 mole) and sulfuric acid (1.5 ml.) in ethanol (400 ml.) is boiled under reflux for 6 hours. About 300 ml. of the ethanol is removed by distillation at reduced pressure. The residue is diluted with 400 ml. of water. The oily ester is taken up in ether, washed with water and brine, and dried over magnesium sulfate. Evaporation of the ether leaves the title compound as an oil which can be purified by distillation in vacuo.

Workup

  1. temperatureunder reflux for 6 hours
  2. customof the ethanol is removed by distillation at reduced pressure
  3. additionThe residue is diluted with 400 ml
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the ether

Sources & evidence

ORD record
ord-cf55b2ce491647c0a5b0b8667929280f
Source dataset
uspto-grants-1979_02
Patent number
US04140861

Reaction notes

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