Thionyl Chloride → 5,7-Dichloro-2,3-dihydro-1H-inden-1-one

HRID 130610ノート

反応式

HRID 130610 の反応式
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13][CH2:14][C:15]([OH:17])=O)[CH:9]=[C:10]([Cl:12])[CH:11]=1>C(Cl)Cl>[Cl:12][C:10]1[CH:9]=[C:8]2[C:7](=[C:6]([Cl:5])[CH:11]=1)[C:15](=[O:17])[CH2:14][CH2:13]2

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 8193053-(3,5-Dichlorophenyl)propionic acid

生成物 1

HCID 222923465,7-Dichloro-2,3-dihydro-1H-inden-1-one収率 71.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Thionyl chloride (45.2 g) was added dropwise at 40° C. to a solution of 3-(3,5-di-chlorophenyl)propionic acid (54.8 g) in methylene chloride (200 ml). After reaction was complete, excess thionyl chloride and the solvent were removed by distillation. The oily residue was added dropwise at 40° C. to a suspension of aluminium chloride (66.7 g) in methylene chloride (200 ml). The reaction mixture was added to dilute hydrochloric acid after 18 hours at 40° C. The aqueous phase was separated off and extracted once with methylene chloride (250 ml). The combined organic phases were freed from the solvent. The residue was recrystallized from cyclohexane. 36 g of a colorless solid (m.p.: 119-120° C.) were obtained.

後処理

  1. customAfter reaction
  2. customexcess thionyl chloride and the solvent were removed by distillation
  3. additionThe oily residue was added dropwise at 40° C. to a suspension of aluminium chloride (66.7 g) in methylene chloride (200 ml)
  4. additionThe reaction mixture was added to dilute hydrochloric acid after 18 hours at 40° C
  5. customThe aqueous phase was separated off
  6. extractionextracted once with methylene chloride (250 ml)
  7. customThe residue was recrystallized from cyclohexane

出典と根拠

ORDレコード
ord-abc7db80ce314183860ea90482ed39a0
出典データセット
uspto-grants-2008_06
特許番号
US07381832B2

反応ノート

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