Acetonitrile → 2-(2-Nitro-4-difluoromethoxybenzoyl)-4,4,6-trimethylcyclohexane-1,3-dione

HRID 1464561ノート

反応式

HRID 1464561 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH3:17][C:18]1([CH3:27])[CH2:23][CH:22]([CH3:24])[C:21](=[O:25])[CH2:20][C:19]1=[O:26].C(#N)C.CC(C)(O)C#N>Cl.C(N(CC)CC)C>[N+:1]([C:4]1[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[CH:10]=[CH:9][C:5]=1[C:6]([CH:20]1[C:19](=[O:26])[C:18]([CH3:17])([CH3:27])[CH2:23][CH:22]([CH3:24])[C:21]1=[O:25])=[O:7])([O-:3])=[O:2]

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 6406Acetone CyanohydrinHCID 147495764,4,6-Trimethylcyclohexane-1,3-dioneHCID 190867612-Nitro-4-difluoromethoxybenzoyl chloride

生成物 1

HCID 190867592-(2-Nitro-4-difluoromethoxybenzoyl)-4,4,6-trimethylcyclohexane-1,3-dione

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8471Triethylamine溶媒

実験手順

5.03 g of 2-nitro-4-difluoromethoxybenzoyl chloride and 2.57 g of 4,4,6-trimethylcyclohexane-1,3-dione are introduced into 20 ml of acetonitrile, and 4.21 g of triethylamine are added dropwise in such a way that the internal temperature does not exceed 40° C. The mixture is subsequently stirred for 15 minutes at room temperature, 1.29 g of acetone cyanohydrin are added, and stirring is continued for 3 hours at room temperature. The reaction mixture is diluted with 100 ml of ethyl acetates and 50 ml of 1N hydrochloric acid are added. After vigorous shaking, the phases are separated, the organic phases are dried over MgSO4, and the solvent is stripped off under reduced pressure. The oil which remains (7.1 g) is chromatographed on silica gel using ethyl acetate/petroleum ether 1:2 as the eluent. This gives 3.28 g (46% of theory) of 2-(2-nitro-4-difluoromethoxy-benzoyl)-4,4,6-trimethylcyclohexane-1,3-dione of melting point 108°-110° C.

後処理

  1. additionare added dropwise in such a way that the internal temperature
  2. customdoes not exceed 40° C
  3. stirringstirring
  4. waitis continued for 3 hours at room temperature
  5. additionare added
  6. customAfter vigorous shaking, the phases are separated
  7. dry with materialthe organic phases are dried over MgSO4
  8. customis chromatographed on silica gel

出典と根拠

ORDレコード
ord-c0d6e47509ab406f8f89d8407c340ab5
出典データセット
uspto-grants-1994_04
特許番号
US05306695

反応ノート

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