Sulfuric Acid → (2,6-Dichloro-4-nitrophenyl)methanol

HRID 746039ノート

反応式

HRID 746039 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[C:13]([Cl:20])[C:9]=1[C:10](Cl)=[O:11].S(=O)(=O)(O)O>C(OCC)C>[Cl:7][C:8]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[C:13]([Cl:20])[C:9]=1[CH2:10][OH:11]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 225716812,6-Dichloro-4-nitrobenzoyl chloride

生成物 1

HCID 23311409(2,6-Dichloro-4-nitrophenyl)methanol収率 26.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Lithium aluminium hydride (400 mg, 10.4 mmol) was added in portions to a stirred solution of 2,6-dichloro-4-nitrobenzoyl chloride (3.0 g, 11.8 mmol) in diethyl ether (50 cm3) at room temperature. After 1.5 h the mixture was poured onto ice (80 g), acidified with 10% sulphuric acid (80 cm3) and extracted with ethyl acetate (3×60 cm3). The dried organic extracts were evaporated to an oil which was purified by chromatography over silica gel with a methanol-dichloromethane solvent gradient. The fractions containing 2,6-dichloro-4-nitrobenzylalcohol, were combined and evaporated under reduced pressure to a give a cream solid mp 111°-4° C. (0.7 g).

後処理

  1. additionAfter 1.5 h the mixture was poured onto ice (80 g)
  2. extractionextracted with ethyl acetate (3×60 cm3)
  3. customThe dried organic extracts were evaporated to an oil which
  4. customwas purified by chromatography over silica gel with a methanol-dichloromethane solvent gradient
  5. additionThe fractions containing 2,6-dichloro-4-nitrobenzylalcohol
  6. customevaporated under reduced pressure to

出典と根拠

ORDレコード
ord-cbd346c2b76c4bf9b973f708636aaa14
出典データセット
uspto-grants-1986_07
特許番号
US04602041

反応ノート

読み込み中…