Nitric Acid → 3,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-one

HRID 53277

反応式

HRID 53277 の反応式
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3]1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][C:7]([N+:13]([O-:15])=[O:14])=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3]1

参加物

4

反応物 2

HCID 944Nitric AcidHCID 3046283,3-Dimethyl-1-indanone

生成物 1

HCID 124417863,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-one

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒2 回

実験手順

To a solution of 3,3-dimethylindan-1-one (LXIV) (16.3 g, 50.9 mmol) (Harms, W. M. and Eisenbraum, E. J. Org. Prep. Proc. Int. 1972, 4, 67-72) in 56 mL of sulfuric acid was slowly added 4.18 mL of 70% nitric acid in 20 mL of sulfuric acid at 0°-5° C. After being stirred for 1 hour, the reaction mixture was poured into 600 g of ice. The precipitates was filtered and washed with water. The solids collected were dissolved in 600 mL of ethyl acetate and washed with NaHCO3 (80 mL×2), dried over magnesium sulfate, and evaporated. The residue was triturated with methanol to give 22.2 g of the title compound as yellow solids; 1H-NMR (CDCl3) δ1.49 (s, 6H), 2.71 (s, 2H), 7.68 (d, J=8.4 Hz, 1H), 8.48 (dd, J=2.0, 8.4 Hz, 1H), 8.53 (d, J=2.0 Hz, 1H); MS m/e 206 (MH+).

後処理

  1. customat 0°-5° C
  2. filtrationThe precipitates was filtered
  3. washwashed with water
  4. customThe solids collected
  5. dissolutionwere dissolved in 600 mL of ethyl acetate
  6. washwashed with NaHCO3 (80 mL×2)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue was triturated with methanol

出典と根拠

ORDレコード
ord-6d49bfe140d74a9fa2e87a5edd1e3425
出典データセット
uspto-grants-1997_04
特許番号
US05618839

関連ノート

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