Phenolate Sodium → 1-Chloro-2-(1-ethylcyclopentyl)-2-phenoxyethylene

HRID 1085653Notes

Reaction equation

HRID 1085653 reaction equation
[C:1]1([O-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[Cl:9][C:10](Cl)=[CH:11][C:12]1([CH2:17][CH3:18])[CH2:16][CH2:15][CH2:14][CH2:13]1>CN1CCCC1=O.C(Cl)Cl>[Cl:9][CH:10]=[C:11]([C:12]1([CH2:17][CH3:18])[CH2:16][CH2:15][CH2:14][CH2:13]1)[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 4445035Phenolate SodiumHCID 132091911-(2,2-Dichlorovinyl)-1-ethylcyclopentane

Product 1

HCID 539991561-Chloro-2-(1-ethylcyclopentyl)-2-phenoxyethyleneYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
210 °C

Procedure

140 g (4.2 mol) of sodium phenolate in 500 ml of N-methylpyrrolidone were heated to 200° C. 116 g (0.6 mol) of 1-(2,2-dichlorovinyl)-1-ethyl-cyclopentane were added dropwise so slowly that the reaction temperature did not fall below 195° C. The mixture was then stirred for a further hour at 210° C. After the mixture had cooled, it was diluted with methylene chloride and extracted several times by shaking with 2N sodium hydroxide solution. The organic phase, which had been dried over sodium sulphate, was concentrated in vacuo, and the residue was fractionated. 132 g (88% of theory) of 1-chloro-2-(1-ethylcyclopentyl)-2-phenoxy-ethylene of boiling point 115° to 125° C./0.1 mm Hg were obtained. ##STR21##

Workup

  1. customdid not fall below 195° C
  2. temperatureAfter the mixture had cooled
  3. extractionextracted several times
  4. stirringby shaking with 2N sodium hydroxide solution
  5. dry with materialThe organic phase, which had been dried over sodium sulphate
  6. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-9f4e914190a54fa7bb7f903ccc869e5b
Source dataset
uspto-grants-1991_04
Patent number
US05010208

Reaction notes

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