Potassium Nitrate → Methyl 4-[3-nitro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylcarbonyl]benzoate

HRID 583059Notes

Reaction equation

HRID 583059 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2.[N+:27]([O-])([O-:29])=[O:28].[K+]>OS(O)(=O)=O>[N+:27]([C:5]1[C:6]([C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=2)=[O:15])=[CH:7][C:8]2[C:9]([CH3:12])([CH3:13])[CH2:10][CH2:11][C:2]([CH3:26])([CH3:1])[C:3]=2[CH:4]=1)([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 10784070Methyl 4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoate

Product 1

HCID 10786864Methyl 4-[3-nitro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylcarbonyl]benzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Compound 43 (693 mg, 1.98 mmol) was dissolved in concentrated H2SO4 (5 ml) and the mixture was added with KNO3 (240 mg, 2.37 mmol) under ice cooling. After 1 hour, the reaction mixture was poured into ice water and extracted with dichloromethane. The organic phase was washed with saturated aqueous solution of sodium hydrogen carbonate, water and saturated brine, and then concentrated after dryness. The residue was recrystallized from ethyl acetate to give methyl 4-[3-nitro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylcarbonyl]benzoate as colorless needles (Compound 44, 414 mg, 53%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase was washed with saturated aqueous solution of sodium hydrogen carbonate, water and saturated brine
  3. concentrationconcentrated after dryness
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a8b3ec7e98de4b3a994e49256735f3c1
Source dataset
uspto-grants-1999_07
Patent number
US05929069

Reaction notes

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