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

HRID 369663Notes

Reaction equation

HRID 369663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:5]=[C:6]([Cl:22])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15](O)[C:16]([C:19]#[N:20])(Cl)[Cl:17].N1C=CC=CC=1.C(OC(=O)C)(=O)C.Cl>CN(C1C=CN=CC=1)C.[Zn].CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:5]=[C:6]([Cl:22])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15]=[C:16]([Cl:17])[C:19]#[N:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 232824233,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-cyano-3,3-dichloro-2-hydroxypropyloxy)butyloxy)benzene

Product 1

HCID 537121863,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-chloro-3-cyano-2-propenyloxy)butyloxy)benzeneYield 83%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.26 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-cyano-3,3-dichloro-2-hydroxypropyloxy)butyloxy)benzene, 0.079 g of pyridine, 0.077 g of acetic anhydride, 10 mg of N,N-dimethyl-4-aminopyridine and 10 ml of N,N-dimethylformamide was stirred at room temperature for 30 minutes, to which 0.065 g of zinc dust was added. The reaction mixture was further stirred at room temperature for 1 hour, poured into 20 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 0.19 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-chloro-3-cyano-2-propenyloxy)butyloxy)benzene (yield, 83%), nD23.0 1.5410.

Workup

  1. additionwas added
  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-a11033ed0c8143d4b9f3fbaf3127a69a
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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