Nitric Acid → 5-Nitro-2,3-dihydro-1-benzofuran

HRID 629676Notes

Reaction equation

HRID 629676 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[N+:10]([O-])([OH:12])=[O:11].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[N+:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 10329DihydrobenzofuranHCID 10340Sodium Carbonate

Product 1

HCID 218165855-Nitro-2,3-dihydro-1-benzofuranYield 14.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

2,3-dihydrobenzofuran (5 g, 41.6 mmol) was dissolved in 35 mL of acetic acid, and ¼ HNO3 (0.9 mL, 45.4 mmol) was added dropwise. At the beginning of reaction, it was heated to 70° C., then the residual HNO3 was added. After 0.5 hour, the reaction was cooled, added into ice-water, and then neutralized with Na2CO3. The water layer was extracted with ethyl acetate. The organic layers were combined and dried, concentrated under vacuum, purified by column chromatography to obtain a product (1 g, 14.6%).

Workup

  1. customAt the beginning of reaction, it
  2. temperaturethe reaction was cooled
  3. extractionThe water layer was extracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated under vacuum
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-e77233f1778e4f70adab9f0514285689
Source dataset
uspto-grants-2016_04
Patent number
US09315513B2

Reaction notes

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