1,2-Dibromoethane → Ethyl 3-(2-bromoethoxy)-2-methylbenzoate

HRID 582821Notes

Reaction equation

HRID 582821 reaction equation
C[O-].[Na+].[OH:4][C:5]1[C:6]([CH3:16])=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:17][CH2:18][CH2:19]Br>C(O)C>[Br:17][CH2:18][CH2:19][O:4][C:5]1[C:6]([CH3:16])=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10942334Sodium MethoxideHCID 15376194Ethyl 3-hydroxy-2-methylbenzoate

Product 1

HCID 15376195Ethyl 3-(2-bromoethoxy)-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

13.6 g (0.2 mol) of sodium methylate are dissolved in 200 ml of ethanol. 36 g (0.2 mol) of ethyl 3-hydroxy-2-methylbenzoate are then added and the mixture refluxed for 2 hours. 61.4 g (0.32 mol) of 1,2-dibromoethane are subsequently added dropwise and the mixture is refluxed for 20 hours. When cold, the reaction mixture is concentrated on a rotary evaporator. The residue is taken up in ethyl acetate and washed 3 times with dilute sodium hydroxide solution. The organic phase is dried and the solvent is distilled off. The product of value is purified by column chromatography. Yield: 14.6 g of oil

Workup

  1. temperaturethe mixture refluxed for 2 hours
  2. temperaturethe mixture is refluxed for 20 hours
  3. concentrationWhen cold, the reaction mixture is concentrated on a rotary evaporator
  4. washwashed 3 times with dilute sodium hydroxide solution
  5. customThe organic phase is dried
  6. distillationthe solvent is distilled off
  7. customThe product of value is purified by column chromatography

Sources & evidence

ORD record
ord-aca5a18da1c74ab3bf1ed27ad8bba621
Source dataset
uspto-grants-1999_07
Patent number
US05925767

Reaction notes

Loading…