Methyl thiocyanate → 4-(4-n-Octylphenyl)-2-cyanophenol

HRID 1492351

反応式

HRID 1492351 の反応式
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].B(Cl)(Cl)Cl.CS[C:28]#[N:29].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>ClCCCl>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:28]#[N:29])[CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

参加物

7

反応物 5

HCID 11168Methyl thiocyanateHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride2 回HCID 140472114'-Octyl-[1,1'-biphenyl]-4-ol

生成物 1

HCID 189501194-(4-n-Octylphenyl)-2-cyanophenol

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

反応条件

温度
80 °C

実験手順

To a suspension of 2.82 g of 4-(4-n-octylphenyl) phenol in 40 ml of 1,2-dichloroethane were added under ice cooling, 6 ml of a solution of boron trichloride (2M) in 1,2-dichloroethane, and then 0.82 ml of methyl thiocyanate and 1.33 g of aluminum chloride. The mixture was stirred at room temperature until the aluminum chloride is dissolved, further stirred for 3 hours at 80° C. and cooled to room temperature. To the resulting mixture was added further 33 ml of 4N-sodium hydroxide solution. The mixture was stirred for 30 minutes at 75° to 80° C. After cooling, the reaction mixture was washed with methylene chloride. The aqueous phase was adjusted to pH2 with 6N hydrochloric acid and extracted with ether. The extract was dried and evaporated under reduced pressure to obtain crude crystals. The crystals were purified by a silica gel column chromatography to give 2.03 g of 4-(4-n-octylphenyl)-2-cyanophenol.

後処理

  1. additionwere added under ice cooling
  2. dissolutionis dissolved
  3. temperaturecooled to room temperature
  4. stirringThe mixture was stirred for 30 minutes at 75° to 80° C
  5. temperatureAfter cooling
  6. washthe reaction mixture was washed with methylene chloride
  7. extractionextracted with ether
  8. customThe extract was dried
  9. customevaporated under reduced pressure
  10. customto obtain crude crystals
  11. customThe crystals were purified by a silica gel column chromatography

出典と根拠

ORDレコード
ord-a6811cdea89441968ceecba62e61f17d
出典データセット
uspto-grants-1994_12
特許番号
US05374373

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