Sulfuric Acid → [(2-Bromoethoxy)(phenyl)methyl]benzene

HRID 1032959Notes

Reaction equation

HRID 1032959 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].S(=O)(=O)(O)O.[CH:10](O)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH:10]([O:4][CH2:3][CH2:2][Br:1])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7037BenzhydrolHCID 108982-Bromoethanol

Product 1

HCID 237821[(2-Bromoethoxy)(phenyl)methyl]benzene

Conditions

Temperature
100 °C

Procedure

To 2-bromoethanol (40.7 g, 326 mmol) was added conc. sulfuric acid (9.96 g, 102 mmol) under ice-cooling while stirring. Thereto was added benzhydrol (12.0 g, 65.1 mmol), and the mixture was heated at 100° C. for 15 minutes. The reaction mixture was allowed to stand for cooling, poured into ice-cold water and extracted with ether. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated. The thus-obtained liquid was distilled under reduced pressure to give the title compound (3). Yield 13.9 g (73%). b.p. 125°-165° C./2.5 mmHg.

Workup

  1. temperaturecooling
  2. temperaturefor cooling
  3. additionpoured into ice-cold water
  4. extractionextracted with ether
  5. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. distillationThe thus-obtained liquid was distilled under reduced pressure

Sources & evidence

ORD record
ord-49430b1a25ba457d9c268629346ac35f
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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