Fuming sulfuric acid → 2,7-Di-t-butylanthraquinone

HRID 278834

反応式

HRID 278834 の反応式
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[C:7]([C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].OS(O)(=O)=O.O=S(=O)=O>C(Cl)Cl>[C:1]([C:5]1[CH:13]=[CH:12][C:8]2[C:9](=[O:10])[C:20]3[C:15](=[CH:16][C:17]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:18][CH:19]=3)[C:14](=[O:21])[C:7]=2[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 2

HCID 24681Fuming sulfuric acidHCID 31062832-Benzoyl-4-tert-butylbenzoic acid

生成物 1

HCID 3576262,7-Di-t-butylanthraquinone収率 138%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
120 °C

実験手順

4-t-Butyl-2-benzoylbenzoic acid 4 (32.0 g, 95 mmol) was placed into a round-bottom flask and oleum (30%, 290 mL) was then added. The reaction mixture turned black and the reaction temperature was increased to 120° C. and stirred for 3 h. The mixture was then poured into ice. The aqueous mixture was extracted using CH2Cl2 (5×), dried over Na2SO4 and concentrated to give a dark solid. This solid was passed through a silica gel column using CH2Cl2 as eluent. After concentrating, the yellow-brown solid was recrystallized from hexane to give product as yellow crystals 21.0 g (69% yield). 1H NMR (CDCl3) δ(ppm): 1.42 (s, 18H), 7.80 (d, J=8.2 Hz, 1H), 7.81 (d, J=8.2 Hz), 8.20 (d, J=8.2 Hz, 1H),), 8.22 (d, J=8.2 Hz, 1H), 8.31 (s, 2H); 13C NMR (CDCl3): 31.01, 35.58, 123.83, 123.90, 127.17, 127.28, 131.08, 131.15, 131.34, 131.42, 133.40, 133.49, 157.94, 158.05, 182.76, 183.28,183.78

後処理

  1. additionThe mixture was then poured into ice
  2. extractionThe aqueous mixture was extracted
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give a dark solid
  6. concentrationAfter concentrating
  7. customthe yellow-brown solid was recrystallized from hexane

出典と根拠

ORDレコード
ord-b2d7745392be45f99609dc14471cb9a7
出典データセット
uspto-grants-2002_03
特許番号
US06361887B1

関連ノート

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