Nitric Acid → HCID 58566315, compound

HRID 445847Notes

Reaction equation

HRID 445847 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]=2[O:3]1.[N+:17]([O-])([OH:19])=[O:18]>FC(F)(F)C(O)=O>[CH3:1][C:2]1([CH3:16])[CH2:6][C:5]2[CH:7]=[C:8]([N+:17]([O-:19])=[O:18])[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 58566309HCID 58566309, compound

Product 1

HCID 58566315HCID 58566315, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (1 g, 4.54 mmol) in trifluoroacetic acid (7 mL) at 0° C. was slowly added nitric acid (1.36 mL). The reaction was stirred at 0° C. for one hour and then at room temperature for 30 minutes. The reaction was added to ice and the resultant solid was collected by filtration, and washed with water to provide ethyl 2,2-dimethyl-5-nitro-2,3-dihydrobenzofuran-7-carboxylate (674) as a yellow solid (1.02 g, 83%).

Workup

  1. customat 0° C.
  2. waitat room temperature for 30 minutes
  3. additionThe reaction was added to ice
  4. filtrationthe resultant solid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-7904f99faa4245929ceba56fb7c687b0
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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