Potassium Carbonate → 1-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)naphthalene

HRID 37318

반응식

HRID 37318 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.[Cl:13][C:14]1[C:15]([CH3:24])=[C:16]([N+:21]([O-:23])=[O:22])[CH:17]=[C:18]([CH3:20])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:13][C:14]1[C:15]([CH3:24])=[C:16]([N+:21]([O-:23])=[O:22])[CH:17]=[C:18]([CH3:20])[C:19]=1[O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Cl:1])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 117874-Chloro-1-naphtholHCID 190729401-Chloro-2,5-dimethyl-3-nitrobenzene

생성물 1

HCID 132459651-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)naphthalene수율 47.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

Into a solution containing 9.10 grams (51.1 mmol) of 4-chloro-1-naphthol and 10.12 grams (46.0 mmol) of 3-chloro-2,5-dimethyl-1-nitrobenzene in 22 milliliters of dimethylsulfoxide at room temperature and under a nitrogen atmosphere was added 8.89 grams (64.4 mmol) of anhydrous potassium carbonate. The resulting mixture was heated to a temperature of 130° C. and maintained at that temperature for a period of 6 hours. The reaction mixture was then filtered and the filtrate was diluted with 20 milliliters of methanol and allowed to cool to room temperature. Crystallization occurred during this cooling period. The filtrate was further cooled in an ice bath, filtered and the collected crystals washed with cold methanol. Recrystallization from a hexane-ethyl acetate mixture afforded 7.92 grams of 3-chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethyl-1-nitrobenzene as a white solid having a melting point of 135° C.-137° C.

후처리

  1. temperaturemaintained at that temperature for a period of 6 hours
  2. filtrationThe reaction mixture was then filtered
  3. additionthe filtrate was diluted with 20 milliliters of methanol
  4. temperatureto cool to room temperature
  5. customCrystallization
  6. waitoccurred during this cooling period
  7. temperatureThe filtrate was further cooled in an ice bath
  8. filtrationfiltered
  9. washthe collected crystals washed with cold methanol
  10. customRecrystallization from a hexane-ethyl acetate mixture

출처 및 근거

ORD 기록
ord-c4ef232cf879414784b333bd904d3bcc
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420163

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