Hydrochloric Acid → 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-chloro-3-ethoxycarbonyl-2-propenyloxy)butyloxy)benzene

HRID 369662

Reaction equation

HRID 369662 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])[CH:14]=[C:13]([Cl:23])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH:11]=O.[Cl:24][C:25](Cl)(Cl)[C:26]([O:28][CH2:29][CH3:30])=[O:27].Cl>[Zn].CN(C)C=O>[Cl:23][C:13]1[CH:14]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:21])[Cl:22])[CH:16]=[C:2]([Cl:1])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH:11]=[C:25]([Cl:24])[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10588Ethyl trichloroacetateHCID 538269084-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde

Product 1

HCID 538327953,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-chloro-3-ethoxycarbonyl-2-propenyloxy)butyloxy)benzeneYield 5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.60 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde, 0.29 g of zinc dust and 10 ml of N,N-dimethylformamide was added ethyl trichloroacetate with stirring at room temperature. After stirring at room temperature for 2 hours, the reaction mixture was poured into 10 ml of diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.04 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-chloro-3-ethoxycarbonyl-2-propenyloxy)butyloxy)benzene (yield, 5%), nD23.0 1.5348.

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. extractionextracted twice with diethyl ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a crude product

Sources & evidence

ORD record
ord-5d15c627687f44229f5bee816b68686d
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Linked notes

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