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

HRID 978476

반응식

HRID 978476 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a95f99a248254827b47c9868e3f65e87
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04665097

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