2-Methoxy-1,4-Naphthoquinone → 2-Methoxy-1,4-diacetyloxynaphthalene

HRID 845544

反応式

HRID 845544 の反応式
[CH3:1][O:2][C:3]1[C:4](=[O:14])[C:5]2[C:10]([C:11](=[O:13])[CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H][H]>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][C:3](=[O:2])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[O:14][C:11](=[O:13])[CH3:10]

参加物

5

反応物 2

HCID 168712-Methoxy-1,4-NaphthoquinoneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 6052732-Methoxy-1,4-diacetyloxynaphthalene

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-methoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the calculated amount of hydrogen was absorbed, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour the catalyst was filtered off and the solvent removed from the filtrate under reduced pressure. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2-methoxy-1,4-diacetyloxynaphthalene, m.p. 135°-136° C.

後処理

  1. customwas absorbed, approximately 4 hours
  2. additionWhile still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture
  3. filtrationwas filtered off
  4. customthe solvent removed from the filtrate under reduced pressure
  5. dissolutionThe residue was dissolved in ether (100 mL)
  6. washwas washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customRecrystallization from ether

出典と根拠

ORDレコード
ord-311bff6d546b4a22b66698e1a70d8775
出典データセット
uspto-grants-1988_07
特許番号
US04758587

関連ノート

読み込み中…