1,2-Dibromoethane → HCID 12725189, compound

HRID 1681864Notes

Reaction equation

HRID 1681864 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Br:9])[C:3]=1[OH:10].[Br:11][CH2:12][CH2:13]Br.[OH-].[K+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Br:9])[C:3]=1[O:10][CH2:13][CH2:12][Br:11]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 17078p-Cresol, 2,6-dibromo-

Product 1

HCID 12725189HCID 12725189, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,6-dibromo-4-methylphenol (18) (26.59 g, 0.1 mol), 1,2-dibromoethane (11.2 ml, 0.13 mol) and potassium hydroxide (8.42 g, 0.15 mol) in 200 ml of absolute ethanol was heated under reflux for 24 hours. The inorganic salt was collected on a filter and the filtrate taken to dryness. The resulting mixture was treated with ethyl ether, chilled, and the solid, which proved to be recovered phenol, collected on a filter. The filtrate was evaporated to afford the ether 19 (24.5 g, 65.7%) as a liquid. This was purified by distillation (0.5 torr, 120°-124° C.) to yield 19.79 g (53.0%) of product. NMR (CDCl3) δ 7.25 (s, 2H, aromatic protons), 3.55-4.38 (m, 4H, 2CH2), and 2.27 (s, 3H, CH3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customThe inorganic salt was collected on
  4. filtrationa filter
  5. additionThe resulting mixture was treated with ethyl ether
  6. temperaturechilled
  7. customto be recovered phenol
  8. customcollected on a filter
  9. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-cb6b1ee651914e24adba788ac1480258
Source dataset
uspto-grants-1992_12
Patent number
US05175173

Reaction notes

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