Nitric Acid → 2,3-Dihydro-2,2-dimethyl-5-nitrobenzofuran

HRID 35690

Reaction equation

HRID 35690 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1([CH3:15])[CH2:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7]1>S(=O)(=O)(O)O>[CH3:5][C:6]1([CH3:15])[CH2:10][C:9]2[CH:11]=[C:12]([N+:1]([O-:4])=[O:2])[CH:13]=[CH:14][C:8]=2[O:7]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 806402,3-Dihydro-2,2-dimethylbenzofuran

Product 1

HCID 142772712,3-Dihydro-2,2-dimethyl-5-nitrobenzofuran

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

During a one hour period an ice cold mixture of 43 mL concentrated nitric acid and 50 mL of concentrated sulfuric acid was added dropwise to 100.0 g (0.67 mole) 2,3-dihydro-2,2-dimethylbenzofuran while maintaining the temperature of 5° C. After complete addition the mixture was stirred at 0° C. for 2.5 hours. The reaction mixture was poured into ice water and the total extracted with diethyl ether. The extract was dried over anhydrous magnesium chloride and filtered. Evaporation of the filtrate under reduced pressure produced a black oil. Purification of this oil by column chromatography on silica gel eluting with toluenen-hexane (9:1), yielded 50.0 g of 2,3-dihydro-2,2-dimethyl-5-nitrobenzofuran as a solid.

Workup

  1. additionAfter complete addition the mixture
  2. extractionthe total extracted with diethyl ether
  3. dry with materialThe extract was dried over anhydrous magnesium chloride
  4. filtrationfiltered
  5. customEvaporation of the filtrate under reduced pressure
  6. customproduced a black oil
  7. customPurification of this oil by column chromatography on silica gel eluting with toluenen-hexane (9:1)

Sources & evidence

ORD record
ord-6afdd7db890342b3a66a6dd63b056309
Source dataset
uspto-grants-1988_08
Patent number
US04767779

Linked notes

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