Water → 2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde

HRID 4668

Reaction equation

HRID 4668 reaction equation
[N+:1]([C:4]1[CH:11]=[C:8]([CH:9]=[O:10])[C:7]([OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17][O:12][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]=1[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 668085-NitrosalicylaldehydeHCID 6421971,4-Dichloro-2-butene, (2E)-

Product 1

HCID 140504962-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehydeYield 43.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8 g of 5-nitrosalicylaldehyde, 30.8 g of trans-1,4-dichloro-2-butene and 13.2 g of potassium carbonate in 35 ml of dimethylformamide was stirred at room temperature for 19 hours, and further stirred at 80°-87° C. (outside temperature) for 2 hours. The mixture was allowed to cool, poured into 80 ml of water, and extracted with chloroform. The extract (organic layer separated) was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The product was eluted with benzene to give 5.3 g of 2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde. (mp. 65°-66° C.).

Workup

  1. temperatureto cool
  2. extractionextracted with chloroform
  3. extractionThe extract
  4. custom(organic layer separated)
  5. concentrationwas concentrated under reduced pressure
  6. washThe product was eluted with benzene

Sources & evidence

ORD record
ord-42e9e6685d48461cbe538debba22bce7
Source dataset
uspto-grants-1988_02
Patent number
US04727082

Linked notes

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