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

HRID 35690ノート

反応式

HRID 35690 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
5 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6afdd7db890342b3a66a6dd63b056309
出典データセット
uspto-grants-1988_08
特許番号
US04767779

反応ノート

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