Propionic Acid → 2-Ethylnaphthoquinone

HRID 1535017ノート

反応式

HRID 1535017 の反応式
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[C:13](O)(=O)[CH2:14]C.S1(CCCC1)(=O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.[N+]([O-])([O-])=O.[Ag+]>[CH2:13]([C:3]1[C:4](=[O:11])[C:5]2[C:10]([C:1](=[O:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:14]

参加物

8

反応物 4

HCID 1032Propionic AcidHCID 85301,4-NaphthoquinoneHCID 31347SulfolaneHCID 62648Ammonium Persulfate

生成物 1

HCID 949222-Ethylnaphthoquinone

試薬・触媒・溶媒 3

HCID 24470Silver Nitrate触媒HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

A solution of 1,4-naphthoquinone (7.91 g), propanoic acid (3.70 g) and silver nitrate (1.53 g) in a mixture of acetonitrile (11.4 mL), sulfolane (34.1 mL) and water (79.5 mL) was heated at 60°-65° C. for 2 hours. A solution of ammonium persulfate (13.7 g) in water (25 mL) was then added dropwise. The mixture was cooled in ice water and extracted with ether. The organic layer was washed with saturated sodium bicarbonate, water and brine, then dried, filtered and evaporated. Chromatography over silica gel afforded 2-ethyl-1,4-naphthoquinone, m.p. 87°-88° C.

後処理

  1. temperaturewas heated at 60°-65° C. for 2 hours
  2. extractionextracted with ether
  3. washThe organic layer was washed with saturated sodium bicarbonate, water and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-234c580e3f164f1398d26ffa028cfc58
出典データセット
uspto-grants-1992_02
特許番号
US05091558

反応ノート

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