2-Methoxynaphthalene → 3-Methoxyacenaphthoquinone

HRID 278963

반응식

HRID 278963 반응식
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].C(=O)=O.C(O)CO.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5]3[C:4]=1[C:13](=[O:17])[C:14](=[O:15])[C:6]=3[CH:7]=[CH:8][CH:9]=2

참가 물질

6

반응물 4

HCID 71192-MethoxynaphthaleneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 86601574Dry ice ethyleneglycol

생성물 1

HCID 22502643-Methoxyacenaphthoquinone수율 67.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 2-methoxynaphthalene (5 g, 31.6 mmol) and oxalyl chloride (11 mL, 126 mmol) in 150 mL of dichloromethane was cooled to −15° C. (CO2/ethylene glycol) under nitrogen. Aluminum trichloride (10.5 g, 79 mmol) was added slowly over 30 minutes. After 3 hours, the mixture was poured onto 100 g of ice. The layers were separated, and the aqueous layer was washed with dichloromethane. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over magnesium sulfate. The solution was concentrated to afford 4.5 g of a solid. The solid was triturated with dichloromethane to give 1.24 g of the title compound as a solid, mp 218-220° C.;

후처리

  1. customThe layers were separated
  2. washthe aqueous layer was washed with dichloromethane
  3. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated

출처 및 근거

ORD 기록
ord-05d9e3fec74d43c59653182e8ac3c7af
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362181B1

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