Phenol → Benzene, (2-bromoethoxy)-

HRID 580104Notes

Reaction equation

HRID 580104 reaction equation
[Br:1][CH2:2][CH2:3]Br.[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+]>O>[O:11]([CH2:3][CH2:2][Br:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Procedure

In a mixed solution consisting of 50 g of 1,2-dibromoethane, 18.5 g of phenol and 100 ml of water was added dropwise 30 ml of water containing therein 7.9 g of sodium hydroxide at a temperature of 130° C. over 30 minutes with stirring, and the reaction solution was further stirred for 6 hours. After completion the reaction, the organic layer was separated from the reaction solution, washed twice with a saturated aqueous potassium carbonate solution, washed twice with water and dried over anhydrous sodium sulfate. The organic layer was separated by filtration and condensed under reduced pressure to give 34.3 g of 2-phenoxyethyl bromide having a boiling point of 105° C. to 107° C. at 6 mmHg in a yield of 85%.

Workup

  1. customAfter completion the reaction
  2. customthe organic layer was separated from the reaction solution
  3. washwashed twice with a saturated aqueous potassium carbonate solution
  4. washwashed twice with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe organic layer was separated by filtration and condensed under reduced pressure

Sources & evidence

ORD record
ord-1bddc2995bc3455ca68d66570f73924c
Source dataset
uspto-grants-1988_06
Patent number
US04751302

Reaction notes

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