Nitric Acid → HCID 67985244, compound

HRID 623663Notes

Reaction equation

HRID 623663 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([O:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:16]=[CH:15][C:14]=1[CH:27]([CH3:29])[CH3:28])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O-])(O)=O.[Na+]>CC(O)=O>[CH2:5]([O:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([N+:1]([O-:4])=[O:2])=[CH:15][C:14]=1[CH:27]([CH3:29])[CH3:28])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 58493444HCID 58493444, compound

Product 1

HCID 67985244HCID 67985244, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

HNO3 (1.11 ml, 13.7 mmol) was added to a suspension of 2,4-bis-benzyloxy-1-isopropyl-benzene (3.8 g, 11.44 mmol) in AcOH (46 ml) and the reaction was heated to 70-80° C. for 40 minutes. The solution was cooled down to 0° C. and neutralized with aq. NaHCO3. The organic phase was extracted with AcOEt and the solvent was removed under reduced pressure. The crude reaction mixture was purified by flash chromatography (PE/AcOEt:95/5 to 90/10) and the title compound was obtained as a yellow solid.

Workup

  1. extractionThe organic phase was extracted with AcOEt
  2. customthe solvent was removed under reduced pressure
  3. customThe crude reaction mixture
  4. customwas purified by flash chromatography (PE/AcOEt:95/5 to 90/10)

Sources & evidence

ORD record
ord-2ba6dd2d465f45c7a9a70ac737939410
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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