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

HRID 1534704

反応式

HRID 1534704 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 solvent evaporated from the filtrate. The residue was dissolved in ether (100 mL), washed with 1M hydrochloric acid (3×50 mL) and then 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. filtrationthe catalyst was filtered off
  4. customsolvent evaporated from the filtrate
  5. dissolutionThe residue was dissolved in ether (100 mL)
  6. washwashed with 1M hydrochloric acid (3×50 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-7b7b659cd2b845afb6ad8d4ef38f3176
出典データセット
uspto-grants-1992_02
特許番号
US05089657

関連ノート

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