1,2-Dibromoethane → 2-(2-Bromoethoxy)naphthalene

HRID 2286258Notes

Reaction equation

HRID 2286258 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][CH2:20]Br>C(C(CC)=O)C>[Br:18][CH2:19][CH2:20][O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 86632-NaphtholHCID 11430Potassium Carbonate

Product 1

HCID 6406922-(2-Bromoethoxy)naphthaleneYield 78%

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Conditions

Temperature
-5 °C

Procedure

A mixture of 144 g (1 mole) of 2-naphthol, 600 ml of diethyl ketone, 275 g (2 moles) of potassium carbonate and 850 g (4.5 moles) of 1,2-dibromoethane is refluxed for 48 hours. Diethyl ketone and excess dibromoethane are then distilled off under reduced pressure and the residue is taken up in 500 ml of methylene chloride and 200 ml of 10% strength sodium hydroxide solution. After the aqueous phase has been separated off, the organic layer is washed with 100 ml of water, dried over sodium sulfate and concentrated under reduced pressure. The solid residue is stirred with 100 ml of n-pentane for 10 minutes at -5° C., filtered and washed with 50 ml of cold pentane. There is obtained 195 g (78% of theory) of pure 1-bromo-2-(2-naphthyloxy)-ethane; m.p.: 93°-95° C.

Workup

  1. temperatureis refluxed for 48 hours
  2. distillationDiethyl ketone and excess dibromoethane are then distilled off under reduced pressure
  3. customAfter the aqueous phase has been separated off
  4. washthe organic layer is washed with 100 ml of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationfiltered
  8. washwashed with 50 ml of cold pentane

Sources & evidence

ORD record
ord-068abdcbf8f7491390646ead278055cd
Source dataset
uspto-grants-1982_04
Patent number
US04327214

Reaction notes

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