1,3-Dioxolane, 4-[(2,4-dinitrophenoxy)methyl]-2,2-dimethyl- → HCID 11128347, compound

HRID 1737126Notes

Reaction equation

HRID 1737126 reaction equation
[N+:1]([C:4]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:5]=1[O:6][CH2:7][CH:8]1[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:5]=1[O:6][CH2:7][CH:8]1[CH2:12][O:11][C:10]([CH3:13])([CH3:14])[O:9]1

Participants

5

Reactant 2

HCID 111092861,3-Dioxolane, 4-[(2,4-dinitrophenoxy)methyl]-2,2-dimethyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 11128347HCID 11128347, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

215 ml of methanol are introduced into a 0.7 l autoclave, 85.3 g (0.3 mole) of 4-(2,4-dinitrophenoxymethyl)-2,2-dimethyl-1,3-dioxolane (step a) are dissolved therein and 0.6 g of palladium on active carbon 10% (Degussa) is added. After the autoclave has been closed and blanketed with nitrogen, hydrogenation is carried out under a pressure of 4 bar and at a temperature of 35 to 40° C. until no more hydrogen is taken up. 1.3 g of active carbon is added under nitrogen to the warm solution and the catalyst is filtered off. 42 g of 70% sulfuric acid are added dropwise to the solution while cooling with ice at 5° C. The product precipitated is filtered off under suction, washed with methanol and dried.

Workup

  1. dissolutionare dissolved
  2. customAfter the autoclave has been closed
  3. addition1.3 g of active carbon is added under nitrogen to the warm solution
  4. filtrationthe catalyst is filtered off
  5. addition42 g of 70% sulfuric acid are added dropwise to the solution
  6. customThe product precipitated
  7. filtrationis filtered off under suction
  8. washwashed with methanol
  9. customdried

Sources & evidence

ORD record
ord-8f0973d921b74fde98f804f1e8baf2ee
Source dataset
uspto-grants-1999_10
Patent number
US05961668

Reaction notes

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