4-Nitrophenol → HCID 10867911, compound

HRID 865405Notes

Reaction equation

HRID 865405 reaction equation
[H-].[Na+].[CH:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5]([OH:12])[CH:4]=1.C([O:16][C:17]([CH3:22])([CH:20]=[CH2:21])[CH2:18]Cl)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.CN(C)C=O>[N+:9]([C:8]1[CH:7]=[CH:6][C:5]([O:12][CH2:18][C:17]([CH3:22])([OH:16])[CH:20]=[CH2:21])=[CH:4][CH:3]=1)([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 13092422HCID 13092422, compound

Product 1

HCID 10867911HCID 10867911, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

Into N,N-dimethyl formamide (200 ml) were suspended 11 g (0.27 mol) of 60%-sodium hydride. With stirring under ice cooling, an N,N-dimethyl formamide (150 ml) solution containing 38 g (0.27 mol) of p-nitrophenol was added dropwise therein over three hours. After the resulting solution was continuously stirred for further one hour as it was, the reaction liquid became a homogeneous yellow solution. The reaction liquid was returned to room temperatures, and an N,N-dimethylformamide (100 ml) solution containing 38 g (0.23 mol) of (1-chloro-2-methyl-3-butene-2-yl) acetate was added dropwise therein over three hours. The resulting mixture was stirred for additional one hour as it was. The reaction liquid was dispersed in water (1,000 ml), and 20 g of potassium carbonate were added therein, followed by stirring for one hour. After the extract obtained by extraction therefrom with ethyl acetate (500 ml) was washed with water and dried, it was concentrated under reduced pressure, thereby obtaining a yellowish brown and oily residue. This residue was purified by chromatography on a silica gel column (ethyl acetate:n-hexane system), whereby 36.5 g of the title compound were obtained. (Yield: 70.8%)

Workup

  1. additionwas added dropwise
  2. stirringAfter the resulting solution was continuously stirred for further one hour as it
  3. customthe reaction liquid
  4. customThe reaction liquid
  5. additionwas added dropwise
  6. waitover three hours
  7. stirringThe resulting mixture was stirred for additional one hour as it
  8. customThe reaction liquid
  9. stirringby stirring for one hour
  10. customAfter the extract obtained by extraction
  11. washwith ethyl acetate (500 ml) was washed with water
  12. customdried
  13. concentrationit was concentrated under reduced pressure
  14. customobtaining a yellowish brown and oily residue
  15. customThis residue was purified by chromatography on a silica gel column (ethyl acetate:n-hexane system)

Sources & evidence

ORD record
ord-2a215f4e4e4143cd91d1d50f6ee7e831
Source dataset
uspto-grants-1996_10
Patent number
US05565586

Reaction notes

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