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

HRID 1016253Notes

Reaction equation

HRID 1016253 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-7ec9d3d2fef149a985bd985ba4973eb8
Source dataset
uspto-grants-2002_11
Patent number
US06476017B2

Reaction notes

Loading…