Potassium Carbonate → 1-(6-Chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone

HRID 1862835Notes

Reaction equation

HRID 1862835 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(#N)C>[Cl:8][C:4]1[N:3]=[C:2]([O:1][CH2:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 204937271-(6-Chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanoneYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 400 g (3.09 moles) of 2-hydroxy-6-chloropyridine and 450 g (3.26 moles) potassium carbonate in 3000 ml acetonitrile was added 551 g (3.08 moles) 1-bromo-3,3-dimethyl-2-butanone. The reaction mixture was stirred at 45°-50° C. for 1.5 hours and then filtered. The solids were washed several times with acetonitrile, the filtrate dried (MgSO4) and the solvent evaporated. Crystallization of the residue from pentane gave 610 g (87% yield) of 1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone. A second recrystallization from pentane gave product melting at 43°-44.5° C.

Workup

  1. filtrationfiltered
  2. washThe solids were washed several times with acetonitrile
  3. dry with materialthe filtrate dried (MgSO4)
  4. customthe solvent evaporated
  5. customCrystallization of the residue from pentane

Sources & evidence

ORD record
ord-2ce76e3f464041f28eeacf1e24050afd
Source dataset
uspto-grants-1979_09
Patent number
US04166854

Reaction notes

Loading…