1,1-Dibromoethane → 2-(2-Bromoethoxy)-1,3-dimethylbenzene

HRID 128204

Reaction equation

HRID 128204 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[OH:11].[Br:12][CH:13](Br)[CH3:14]>O.C(O)C>[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[O:11][CH2:14][CH2:13][Br:12]

Participants

6

Reactant 3

HCID 112011,1-DibromoethaneHCID 113352,6-DimethylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 24522082-(2-Bromoethoxy)-1,3-dimethylbenzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution containing sodium hydroxide (80 g) in water (1 liter) and ethanol (0.5 liter) are added 2,6-dimethyl-phenol (245 g) dissolved in ethanol (0.5 liter), and then dibromoethane (750 g). The mixture is refluxed for 48 hours, under vigorous stirring. It is then extracted with methylene chloride. After washing with dilute aqueous sodium hydroxide and then with water, the solvent is evaporated in vacuo. 2(2,6-Dimethyl-phenoxy)-1-bromo-ethane boils at 148°-150° C./25 mm Hg.

Workup

  1. temperatureThe mixture is refluxed for 48 hours, under vigorous stirring
  2. extractionIt is then extracted with methylene chloride
  3. washAfter washing with dilute aqueous sodium hydroxide
  4. customwith water, the solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-7b9296f09277488298a19d66a77727f6
Source dataset
uspto-grants-1981_03
Patent number
US04259334

Linked notes

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