3-Methyl-4-nitrobut-2-en-1-ol → HCID 54574485, compound

HRID 1856493Notes

Reaction equation

HRID 1856493 reaction equation
[N+:1]([CH2:4][C:5]([CH3:9])=[CH:6][CH2:7][OH:8])([O-:3])=[O:2].CC(C)=[O:12].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[N+:1]([CH2:4][C:5]([CH3:9])=[CH:6][C:7]([OH:12])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 544391273-Methyl-4-nitrobut-2-en-1-olHCID 131709961Jones' reagent

Product 1

HCID 54574485HCID 54574485, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 0.1 Mol of 4-Nitro-3-methyl-2-butenol in acetone at 10°-15° was titrated with approximately 0.26 Mol of Jones reagent until the reaction mixture stayed dark orange colored. After 2 hours stirring at 10°-15° C. the mixture was decanted from the green chromium salts and the acetone removed. The residue was dissolved in ether and washed several times with saturated NaCl solution. After evaporation, the residue was crystallized from hot benzene and off-white crystals, mp 85°, were obtained. Two more recrystallizations from benzene yielded the pure nitroacid, mp 100°-102°.

Workup

  1. customat 10°-15°
  2. customwas decanted from the green chromium salts
  3. customthe acetone removed
  4. dissolutionThe residue was dissolved in ether
  5. washwashed several times with saturated NaCl solution
  6. customAfter evaporation
  7. customthe residue was crystallized from hot benzene and off-white crystals, mp 85°
  8. customwere obtained
  9. customTwo more recrystallizations from benzene
  10. customyielded the pure nitroacid, mp 100°-102°

Sources & evidence

ORD record
ord-b92c4a263a0b44fbbe3217402720a7d3
Source dataset
uspto-grants-1980_08
Patent number
US04219660

Reaction notes

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