Sodium Hydroxide → HCID 54325626, compound

HRID 1414585Notes

Reaction equation

HRID 1414585 reaction equation
[C:1]1([C:7](=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[Cl:12])[CH:8]=[N:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CC1C=CC=CC=1.S(Cl)(O)(=O)=O>C1COCC1>[C:1]1([C:7](=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=2)[Cl:12])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 22723482HCID 22723482, compoundHCID 86734362HCID 86734362, compound

Product 1

HCID 54325626HCID 54325626, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2g of 2-phenyl-3-(4-bromophenyl)-3-chloro-acrylaldoxime (5.9 m moles) were suspended in 50 ml of THF. The mixture was cooled to 0° C and, successively, 5 ml of sodium hydroxide solution and 1.14 g of p-toluene-sulfochloride were added. The mixture was stirred for 1 hour at 10° C and evaporated at room temperature. The solid residue was taken up with a small amount of methylene chloride and applied onto a column with basic aluminum oxide in n-hexane. Elution was effected with petroleum ether and then with methylene chloride. In this way pure 2-phenyl-3-(4-bromophenyl)-3-chloro-acrylonitrile (melting point: 128° -130° C) was obtained.

Workup

  1. customevaporated at room temperature
  2. washElution

Sources & evidence

ORD record
ord-9f8c51ed10c246458dfd37e4ceeeec64
Source dataset
uspto-grants-1977_01
Patent number
US04001431

Reaction notes

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