1,2-Dibromoethane → HCID 12725189, compound

HRID 477493Notes

Reaction equation

HRID 477493 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-d7b47b653e2046e09dcb848af2ba5bbc
Source dataset
uspto-grants-1989_12
Patent number
US04888353

Reaction notes

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