2,4-Dichlorophenol → HCID 54380887, compound

HRID 569197Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][O-:11].[Na+].Cl[C:14](Cl)=[CH:15][C:16]([CH3:21])([CH3:20])[CH2:17][CH2:18][Cl:19]>CN1CCCC1=O.C(Cl)Cl>[Cl:19][C:18]([O:11][C:10]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[Cl:8])=[CH:17][C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 200 °C

Procedure

489 g (3 mols) of 2,4-dichlorophenol are dissolved in 1.2 liters of N-methylpyrrolidone, and 600 ml (3 mols) of a 30% strength solution of sodium methylate are added. Methanol and 200 ml of N-methylpyrrolidone are distilled off at 20 mbar. 201 g (1 mol) of 1,1,5-trichloro-3,3-dimethyl-1-pentene are slowly added dropwise at 200° C. and atmospheric pressure. The mixture is then stirred at 200° C. for 6 hours. The solution obtained is diluted with methylene chloride and extracted by shaking several times with dilute sodium hydroxide solution. The dried solution is evaporated and the remaining solvent removed at 0.1 mbar and 150° C. 410 g (90% of theory) of 1-chloro-3,3-dimethyl-1,5-di(2,4-dichlorophenoxy)-1-pentene are obtained as an oil.

Workup

distillationMethanol and 200 ml of N-methylpyrrolidone are distilled off at 20 mbar
customThe solution obtained
extractionextracted
stirringby shaking several times with dilute sodium hydroxide solution
customThe dried solution is evaporated
customthe remaining solvent removed at 0.1 mbar and 150° C

Sources & evidence

ORD record: ord-0b218d654f2e44f499bd7db7040ba10e
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04731452

Reaction notes

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