Thioanisole → HCID 18183648、化合物

HRID 1358164ノート

反応式

HRID 1358164 の反応式
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:13](Cl)(=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[CH3:8][S:7][C:1]1[CH:6]=[CH:5][C:4]([C:13](=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([C:4]2[CH:5]=[CH:6][C:1]([S:7][CH3:8])=[CH:2][CH:3]=2)=[O:22])=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 7520ThioanisoleHCID 67165Azelaoyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 18183648HCID 18183648、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Thioanisole (23.5 ml, 0.20 mol) is added to a suspension of AlCl3 (27.3 g, 0.205 mol) in 200 ml of CH2Cl2. Azelaoyl chloride (19.7 ml, 0.10 mol) is added dropwise slowly, while the reaction mixture is cooled in an ice bath and the reaction solution is stirred for 19 h at room temperature. Then, the reaction solution is poured into ice-water. The produced white precipitate is filtered off and the crude product is extracted from the filtrate with CH2Cl2, washed with brine, dried over MgSO4, and concentrated. The residue is purified by recrystallization from i-Pr2O—CHCl3. The product is obtained as a white solid. 1H NMR (CDCl3), δ[ppm]: δ1.35-1.43 (m, 6H), 1.72 (t, 4H), 2.52 (s, 6H), 2.91 (t, 4H), 7.26 (d, 4H), 7.87 (d, 4H)

後処理

  1. temperatureis cooled in an ice bath
  2. filtrationThe produced white precipitate is filtered off
  3. extractionthe crude product is extracted from the filtrate with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by recrystallization from i-Pr2O—CHCl3
  8. customThe product is obtained as a white solid

出典と根拠

ORDレコード
ord-1a3f8dce87414f3e8ab420e2cca79879
出典データセット
uspto-grants-2003_07
特許番号
US06596445B1

反応ノート

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