Pyridine → HCID 86738931, compound

HRID 2166838Notes

Reaction equation

HRID 2166838 reaction equation
[CH3:1][C:2]1([CH3:12])[C@H:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[C@@H:3]1[C:9](Cl)=[O:10].[Cl:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[CH2:22][OH:23])=[CH:16][CH:15]=1.N1C=CC=CC=1>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[C@H:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[C@@H:3]1[C:9]([O:23][CH2:22][C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([O:18][C:17]2[CH:27]=[CH:28][C:14]([Cl:13])=[CH:15][CH:16]=2)[CH:20]=1)=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4281345[3-(4-chlorophenoxy)phenyl]methanolHCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chloride

Product 1

HCID 86738931HCID 86738931, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 20 ml of dry benzene was dissolved 2.28 g of cis-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarbonyl chloride, followed by addition of 2.34 g of 3-(4-chlorophenoxy)benzyl alcohol and 1.58 g of pyridine. The mixture was stirred at room temperature overnight. Thereafter, the reaction mixture was washed with dilute hydrochloric acid and water, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove a low-boiling fraction, whereby an oily product was obtained as a residue. This oil was purified by preparative liquid chromatography [column: Waters Associates' Prep LC/System 500, Prep PAK® 500/SILICA; solvent system: diisopropyl ether:n-hexane=6:94, v/v]. The above procedure yielded 3.91 g of 3-(4-chlorophenoxy)benzyl cis-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (yield 92%).

Workup

  1. washThereafter, the reaction mixture was washed with dilute hydrochloric acid and water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove a low-boiling fraction, whereby an oily product
  5. customwas obtained as a residue
  6. customThis oil was purified by preparative liquid chromatography [column: Waters Associates' Prep LC/System 500, Prep PAK® 500/SILICA; solvent system: diisopropyl ether:n-hexane=6:94, v/v]

Sources & evidence

ORD record
ord-20c9837e042b4a21babda9ac1b4dfca8
Source dataset
uspto-grants-1983_06
Patent number
US04389412

Reaction notes

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