N-methyl-2-pyrrolidone → [(1-Chloro-3,3,4-trimethylpent-1-en-2-yl)oxy]benzene

HRID 1253129Notes

Reaction equation

HRID 1253129 reaction equation
[C:1]1([O-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].CN1CCCC1=O.[Cl:16][C:17](Cl)=[CH:18][C:19]([CH3:24])([CH3:23])[CH:20]([CH3:22])[CH3:21]>C(Cl)Cl>[Cl:16][CH:17]=[C:18]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:19]([CH3:24])([CH3:23])[CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 4445035Phenolate SodiumHCID 132952241,1-Dichloro-3,3,4-trimethylpent-1-ene

Product 1

HCID 54514707[(1-Chloro-3,3,4-trimethylpent-1-en-2-yl)oxy]benzeneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

487 g of sodium phenolate are introduced into 1.6 liters of N-methylpyrrolidone at about 100° C., and dissolved by heating the mixture to 200° C. 360 g (2 mols) of 1,1-dichloro-3,3,4-trimethyl-pent-1-ene are added dropwise in the course of 3 hours at a rate such that the temperature of the reaction mixture does not fall below 195° C. Thereafter, the mixture is heated at 200°-210° C. for 8 hours. Working-up is carried out by diluting the solution with methylene chloride and extracting it by shaking withh dilute sodium hydroxide solution. After drying and stripping off the solvent, 406 g of crude product remain, this product being distilled at 105°-120° C./0.1 mbar. 337 g (71% of theory) of 1-chloro-2-phenoxy-3,3,4-trimethyl-pent-1-ene are obtained. ##STR18##

Workup

  1. dissolutiondissolved
  2. customdoes not fall below 195° C
  3. temperatureThereafter, the mixture is heated at 200°-210° C. for 8 hours
  4. extractionextracting it
  5. customAfter drying
  6. distillationthis product being distilled at 105°-120° C./0.1 mbar

Sources & evidence

ORD record
ord-35e6bdee1bb34e1aa34a6016da6887ce
Source dataset
uspto-grants-1988_05
Patent number
US04747869

Reaction notes

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