Nitric Acid → 2,2-Dimethyl-6-nitro-2,3-dihydro-4H-1-benzopyran-4-one

HRID 1722051ノート

反応式

HRID 1722051 の反応式
[CH3:1][C:2]1([CH3:13])[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3]1.[N+:14]([O-])([OH:16])=[O:15].O>S(=O)(=O)(O)O>[N+:14]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:13])([CH3:1])[CH2:11][C:10]2=[O:12])([O-:16])=[O:15]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 962WaterHCID 74542902,2-Dimethyl-chroman-4-one

生成物 1

HCID 147733892,2-Dimethyl-6-nitro-2,3-dihydro-4H-1-benzopyran-4-one

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒2 回

実験手順

2,2-Dimethylchroman-4-one (4 g, 23.2 mmol) was added portionwise over 10 minutes to 7 ml of concentrated sulfuric acid at 0°-5° C., then cooled in an acetone-ice bath as concentrated nitric acid (s.g. 1.5, 90%, 1.4 ml) in 3 ml concentrated sulfuric acid was added dropwise over 20 minutes. The resulting mixture was poured into 100 ml ice and water and extracted 2×50 ml ethyl acetate. The organic layers were combined, washed 4×50 ml water and then brine, dried over magnesium sulfate, stripped to solids (5.3 g) and chromatographed on 500 g silica gel, gradiently eluting with 20:1, 15:1, 10:1 and finally 5:1 hexane:diethyl ether to yield title product as a white solid, 2.1 g (39%); tlc Rf 0.3 (1:1 diethyl ether:hexane); m/e 221(P+), 206, 166, 120.

後処理

  1. additionwas added dropwise over 20 minutes
  2. extractionextracted 2×50 ml ethyl acetate
  3. washwashed 4×50 ml water
  4. dry with materialbrine, dried over magnesium sulfate
  5. customchromatographed on 500 g silica gel
  6. washgradiently eluting with 20:1, 15:1, 10:1 and finally 5:1 hexane

出典と根拠

ORDレコード
ord-4cec2150f8654930aac51f1f63d0212a
出典データセット
uspto-grants-1989_08
特許番号
US04853410

反応ノート

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