Potassium Carbonate → 4-[(6-Bromohexyl)oxy]benzonitrile

HRID 359787Notes

Reaction equation

HRID 359787 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>[I-].[Na+].CC(C)=O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 130194-Cyanophenol

Product 1

HCID 134508844-[(6-Bromohexyl)oxy]benzonitrileYield 70.9%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 23.8 g (0.2 mole) of 4-cyanophenol, 55.3 g (0.4 mole) of milled potassium carbonate, 97.6 g of 1,6-dibromohexane, 0.5 g of sodium iodide and 750 ml of acetone was stirred at reflux for two days. The solid was filtered off and the filtrate concentrated in vacuo. The residue was partitioned between water and methylene dichloride, and the organic phase was dried and concentrated. The residue was distilled to give 40 g of 4-(6-bromohexyloxy)benzonitrile, b.p. 150°-160° C. (0.05 mm).

Workup

  1. temperatureat reflux for two days
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was partitioned between water and methylene dichloride
  5. customthe organic phase was dried
  6. concentrationconcentrated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-ca35385afa284f28b23647dec32a4aa0
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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