2-Methyl-2-(4-nitrophenyl)-1,3-dioxolane → HCID 67491648, compound

HRID 1921677Notes

Reaction equation

HRID 1921677 reaction equation
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1>CO>[CH3:1][C:2]1([CH:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)[O:3][CH2:4][CH2:5][O:6]1

Participants

3

Reactant 1

HCID 6065982-Methyl-2-(4-nitrophenyl)-1,3-dioxolane

Product 1

HCID 67491648HCID 67491648, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.37 g (40 mmol) of 2-methyl-2-(4-nitrophenyl)-[1,3]dioxolane is placed in 160 mL of methanol and hydrogenated with 1.00 g of Nishimura catalyst at ambient temperature under a pressure of 50 psi. Then the catalyst is filtered off and the filtrate is concentrated by evaporation. The residue is dissolved in cyclohexane, filtered to remove insoluble matter, and the filtrate is evaporated to dryness. Yield: 7.00 g (94%), cis/trans ratio 77:23; NMR: LG201616.

Workup

  1. filtrationThen the catalyst is filtered off
  2. concentrationthe filtrate is concentrated by evaporation
  3. dissolutionThe residue is dissolved in cyclohexane
  4. filtrationfiltered
  5. customto remove insoluble matter
  6. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-da2aaafd03fc46508654e7b5817da859
Source dataset
uspto-grants-2012_05
Patent number
US08173699B2

Reaction notes

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