Potassium Carbonate → 4-Chloro-5-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-nitrotoluene

HRID 978476

反応式

HRID 978476 の反応式
[Cl:1][C:2]1[C:7](Cl)=[CH:6][C:5]([CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Cl:13][C:14]1[C:23]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=2[C:17]([OH:24])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:7]([O:24][C:17]2[C:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=3[C:14]([Cl:13])=[CH:15][CH:16]=2)=[CH:6][C:5]([CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 3437951,2-Dichloro-4-methyl-5-nitrobenzeneHCID 202033334-Chloro-5,6,7,8-tetrahydronaphthalen-1-ol

生成物 1

HCID 132459894-Chloro-5-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-nitrotoluene収率 98.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

To a solution containing 39.96 g of 4,5-dichloro-2-nitrotoluene and 39.30 g of 4-chloro-5,6,7,8-tetrahydro-1-naphthol in 250 ml of DMF under an atmosphere of nitrogen and at room temperature was added 3.87 g of anhydrous potassium carbonate. The resulting mixture was then heated to 110° C. After 20 hrs at 110° C., the reaction mixture was cooled to room temperature. The DMF was removed in vacuo. The residue was dissolved in 500 ml of warm toluene and filtered through celite. The filter cake was thoroughly washed with toluene. The solvents from the combined filtrates were removed to afford 67.04 g of tan powder. This material was recrystallized from a hexane-ethyl acetate mixture to afford 49.46 g of the desired product as light tan crystals. mp 139°-140° C. NMR (CDCl3): 1.6-1.9 (m, 4H), 2.4-2.9 (m, 7H, contains singlet at 2.45), 6.51 (s, 1H), 6.73 (d, J-8 Hz, 1H), 7.18 (d, J=8 Hz, 1H), 8.15 (s, 1H).

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customThe DMF was removed in vacuo
  3. dissolutionThe residue was dissolved in 500 ml of warm toluene
  4. filtrationfiltered through celite
  5. washThe filter cake was thoroughly washed with toluene
  6. customThe solvents from the combined filtrates were removed

出典と根拠

ORDレコード
ord-a95f99a248254827b47c9868e3f65e87
出典データセット
uspto-grants-1987_05
特許番号
US04665097

関連ノート

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