Nitric Acid → 3'-Nitrobutyrophenone

HRID 1826452

反応式

HRID 1826452 の反応式
[N+:1]([O-:4])(O)=[O:2].[C:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])[CH2:6][CH2:7][CH3:8].[N+]([O-])(O)=O.S(=O)(=O)(O)O>S(=O)(=O)(O)O>[N+:1]([C:12]1[CH:11]=[C:10]([C:5](=[O:9])[CH2:6][CH2:7][CH3:8])[CH:15]=[CH:14][CH:13]=1)([O-:4])=[O:2]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 10315ButyrophenoneHCID 71777668Sulfuric acid, mixt. with nitric acid

生成物 1

HCID 1427473'-Nitrobutyrophenone収率 10%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒3 回

反応条件

温度
-5 °C

実験手順

Concentrated nitric acid (40 ml) was added cautiously with cooling to concentrated sulphuric acid (100 ml) maintaining a temperature of −5° C. Another solution of butyrophenone (59.2 g, 0.47 mol) in concentrated sulphuric acid (140 ml) was made up with shaking, keeping the temperature at −5° C. (+/−5° C.). The former nitric acid/sulphuric acid solution was added portionwise over 45 min to the latter solution of ketone in sulphuric acid keeping the temperature at −10° C.(+/−5° C. during the addition and for a subsequent 30 min. The reaction mixture was poured onto crushed ice (1.5 l) and then extracted with diethyl ether (200 ml and then 3×100 ml). The combined organic extracts were washed with water and then aqueous saturated sodium hydrogen carbonate solution and dried (MgSO4) before concentrating in vacuo. The crude yellow oil crystallised after 16 h and was then purified by chromatography on silica gel (1 kg) eluting with hexane:diethyl ether (9:1) to give the title compound as a white solid (9.1 g, 10%).

後処理

  1. customat −5° C.
  2. custom(+/−5° C.)
  3. additionduring the addition
  4. additionThe reaction mixture was poured
  5. extractionextracted with diethyl ether (200 ml
  6. washThe combined organic extracts were washed with water
  7. dry with materialaqueous saturated sodium hydrogen carbonate solution and dried (MgSO4)
  8. concentrationbefore concentrating in vacuo
  9. customThe crude yellow oil crystallised after 16 h
  10. customwas then purified by chromatography on silica gel (1 kg)
  11. washeluting with hexane:diethyl ether (9:1)

出典と根拠

ORDレコード
ord-13469da1c5d34533ac792ed1aaee33bc
出典データセット
uspto-grants-2006_05
特許番号
US07049444B2

関連ノート

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