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

HRID 629690Notes

Reaction equation

HRID 629690 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)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

4

Reactant 2

HCID 944Nitric AcidHCID 10329Dihydrobenzofuran

Product 1

HCID 218165855-Nitro-2,3-dihydro-1-benzofuranYield 44.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

2,3-Dihydrobenzofuran (36 g, 0.3 mol) was added to glacial acetic acid (100 mL), heated to 65° C., then concentrated nitric acid (25 mL, 0.36 mol) was added dropwise into the reaction solution, the temperature of the reaction solution was controlled at 65-75° C. After the end of dropwise addition, the agitation was kept for 0.5 h. It was then cooled to room temperature, filtered, washed with water, and dried to obtain a product (22 g, 44.4%).

Workup

  1. customwas controlled at 65-75° C
  2. additionAfter the end of dropwise addition
  3. temperatureIt was then cooled to room temperature
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-1435d280bf704d4a8d28c9d6bbecc22e
Source dataset
uspto-grants-2016_04
Patent number
US09315513B2

Reaction notes

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