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

HRID 1534704

반응식

HRID 1534704 반응식
[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]

참가 물질

5

반응물 2

HCID 168712-Methoxy-1,4-NaphthoquinoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 6052732-Methoxy-1,4-diacetyloxynaphthalene

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7b7b659cd2b845afb6ad8d4ef38f3176
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05089657

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