Potassium Carbonate → 4-(4-Cyanophenoxy)-1-chloro-2-butene

HRID 1596473

Reaction equation

HRID 1596473 reaction equation
[Cl:1][CH:2]=[CH:3][CH2:4][CH2:5]Cl.[C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)#[N:8].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:5][CH:4]=[CH:3][CH2:2][Cl:1])=[CH:11][CH:10]=1)#[N:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 35801CID 35801

Product 1

HCID 541838494-(4-Cyanophenoxy)-1-chloro-2-butene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,4-Dichlorobutene (750 g; 5 mol) was added to a stirred suspension of 4-cyanophenol (119.12 g; 1 mol) and K2CO3 (345 g; 2.5 mol) in MeCN (1000 mL) and the reaction mixture was refluxed for 4 h. The reaction mixture was filtered and concentrated. The residue was dissolved in di-iso-propyl ether (2000 mL) and after 24 h the precipitate was filtered off. The filtrate was concentrated giving the sub-title compound as a yellow oil which solidified upon standing (186 g; 0.89 mol).

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in di-iso-propyl ether (2000 mL) and after 24 h the precipitate
  5. filtrationwas filtered off
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b79b5f76dddd400c9cf05b02899119b2
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Linked notes

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