Chloroform → HCID 13101302, compound

HRID 2295971Notes

Reaction equation

HRID 2295971 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][C:11]([CH3:13])=[CH2:12].[OH-].[Na+].[CH:19]([Cl:22])(Cl)[Cl:20]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][C:11]1([CH3:13])[CH2:12][C:19]1([Cl:22])[Cl:20]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 13101307HCID 13101307, compound

Product 1

HCID 13101302HCID 13101302, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Into a solution of 17 g of 3-chloro-4-(3-methyl-3-butenyloxy)nitrobenzene and 0.4 g of tetra-n-butylammonium bromide in chloroform (29.4 g), a 50% sodium hydroxide solution (78.2 g) was dropwise added while stirring at room temperature, and stirring was continued at 50° C. for 2.5 hours. The resultant mixture was poured into ice-water and extracted with chloroform. The extract was concentrated under reduced pressure, and the precipitated crystals were subjected to filtration by a glass filter and washed with ether to give 19.4 g of 3-chloro-4-[2-(1-methyl-2,2-dichlorocyclopropyl)ethoxy]nitrobenzene.

Workup

  1. stirringstirring
  2. extractionextracted with chloroform
  3. concentrationThe extract was concentrated under reduced pressure
  4. filtrationthe precipitated crystals were subjected to filtration by a glass
  5. filtrationfilter
  6. washwashed with ether

Sources & evidence

ORD record
ord-16ae591be4aa456fbd5c2b8c18fefddf
Source dataset
uspto-grants-1984_01
Patent number
US04427596

Reaction notes

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