Nitric Acid → HCID 12712917, compound

HRID 466322Notes

Reaction equation

HRID 466322 reaction equation
[CH3:1][Si:2]([C:5]1[C:6]([Si](C)(C)C)=[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:9][CH:10]=1)([CH3:4])[CH3:3].[N+:19]([O-])([OH:21])=[O:20].[OH-].[Na+]>C(OC(=O)C)(=O)C>[N+:19]([C:9]1[CH:10]=[C:5]([Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:6]=[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 54094722HCID 54094722, compound

Product 1

HCID 12712917HCID 12712917, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

To a solution of 1.18 g (4.00 mmol) of sym-tris(trimethylsilyl)benzene in 1.7 ml of acetic anhydride was added a solution of 0.4 ml (9.1 mmol) of 94% nitric acid in 1.7 ml of acetic anhydride at -10° C. The mixture was stirred at 10° to -5° C. for 2 hours and then at room temperature for 22 hours. The reaction mixture was poured into sodium hydroxide solution and the aqueous solution was extracted with methylene chloride. The extract was evaporated. The residue was purified by column chromatography on silica gel [eluent: petroleum ether] to give 636 mg of pale yellow crystals, m.p. 86°-87° C. (yield 59%). 1H-NMR spectrum δ(CDCl3)ppm: 0.33 (18H,s), 7.90 (1H,t,J=1.1 Hz), 8.29 (2H,d,J=1.1 Hz).

Workup

  1. waitat room temperature for 22 hours
  2. extractionthe aqueous solution was extracted with methylene chloride
  3. customThe extract was evaporated
  4. customThe residue was purified by column chromatography on silica gel [eluent: petroleum ether]

Sources & evidence

ORD record
ord-275c615db9a14399bb829f3397b813b4
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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