2-Methoxynaphthalene → 3-Methoxyacenaphthoquinone

HRID 566975

反応式

HRID 566975 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 22502643-Methoxyacenaphthoquinone収率 67.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.; 1H NMR (DMSO-d6): δ8.38 (d, 1H), 8.25 (d, 1H), 7.90 (d, 1H), 7.63 (m, 2H), 4.07 (s, 3H).

後処理

  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

出典と根拠

ORDレコード
ord-3a13157bbb5f4060a050e2da0fa024e0
出典データセット
uspto-grants-2001_01
特許番号
US06177423B1

関連ノート

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