Nitric Acid → HCID 15712739, compound

HRID 703514Notes

Reaction equation

HRID 703514 reaction equation
[CH:1]([CH:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)C>[CH:1]([CH:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15660880HCID 15660880, compound

Product 1

HCID 15712739HCID 15712739, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-isopropyl-7-phenylheptanoic acid (1.0 g; prepared as the intermediate for the compound of example 1 (b)) was dissolved in anhydrous acetic acid (5ml). The solution was cooled in an ice-bath. Fuming nitric acid (0.4 ml) was dropped into the solution. The solution was stirred for 30 mins. Anhydrous acetic acid was quenched by adding potassium hydroxide to the reaction solution. The reaction solution adjusted to pH 6.0~7.0 was extracted with ethyl acetate. The ethyl acetate layer separated was washed with water, followed by saturated brine, dried and then evaporated. The residue was purified by column chromatography on silica gel to give the title compound (850 mg) having the following physical data:

Workup

  1. temperatureThe solution was cooled in an ice-bath
  2. customAnhydrous acetic acid was quenched
  3. additionby adding potassium hydroxide to the reaction solution
  4. extractionwas extracted with ethyl acetate
  5. customThe ethyl acetate layer separated
  6. washwas washed with water
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2bbe43ce7dd54412b4a6a8957a6d60bf
Source dataset
uspto-grants-1991_01
Patent number
US04983624

Reaction notes

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