2,4-Dichlorobenzyl chloride → 3,3-Dimethylbutyl-2,4-dichlorobenzyl-pyridin-3-yl-carbinol

HRID 1388504Notes

Reaction equation

HRID 1388504 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Cl.ClC(Cl)(Cl)C1C=CC=CC=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([CH2:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:28])[CH:22]=1.[NH4+].[Cl-]>CCOCC.BrBr>[CH3:32][C:31]([CH3:34])([CH3:33])[CH2:30][CH2:29][C:27]([CH2:4][C:3]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=1[Cl:1])([C:23]1[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=1)[OH:28]

Participants

7

Reactant 4

HCID 72122,4-Dichlorobenzyl chloride2×HCID 7367BenzotrichlorideHCID 25517Ammonium ChlorideHCID 131209213,3-Dimethylbutyl pyridin-3-yl ketone

Product 1

HCID 131209233,3-Dimethylbutyl-2,4-dichlorobenzyl-pyridin-3-yl-carbinol

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 66.2 g of 2,4-dichlorobenzyl chloride in 150 ml of ether was added dropwise to 8.2 g of Mg in 100 ml of diethyl ether. After 20% of the amount of dichlorobenzyl chloride had been added, the reaction was started by adding a few drops of bromine. After completion of the dropwise addition of the 2,4-dichlorobenzyl chloride solution, the mixture was refluxed for 1/2 an hour. It was then added dropwise to a solution of 55 g of 3,3-dimethylbutyl pyridin-3-yl ketone in 100 ml of ether. After it had been refluxed for a further two hours, the reaction mixture was hydrolyzed by dropwise addition of saturated aqueous NH4Cl solution (until the pH was 8), while being cooled with ice. The mixture was stirred for 15 hours at room temperature (20° C.) and extracted with diethyl ether, and the ether phase was washed with water, dried over Na2SO4, concentrated and distilled. 52 g of 3,3-dimethylbutyl-2,4-dichlorobenzyl-pyridin-3 -yl-carbinol (active ingredient No. 36) were obtained; boiling point 196°-202° C./0.5 mbar.

Workup

  1. temperaturethe mixture was refluxed for 1/2 an hour
  2. temperatureAfter it had been refluxed for a further two hours
  3. temperaturewhile being cooled with ice
  4. extractionextracted with diethyl ether
  5. washthe ether phase was washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. distillationdistilled
  9. custom36) were obtained

Sources & evidence

ORD record
ord-4941fa4b9c754e2ba9e40ac3c426c774
Source dataset
uspto-grants-1984_02
Patent number
US04431812

Reaction notes

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