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

HRID 746039노트

반응식

HRID 746039 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cbd346c2b76c4bf9b973f708636aaa14
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04602041

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