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

HRID 37318

反応式

HRID 37318 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c4ef232cf879414784b333bd904d3bcc
出典データセット
uspto-grants-1995_05
特許番号
US05420163

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