Hydroquinone → 4-(3-Chloro-5-nitro-phenoxy)-phenol

HRID 2197946

反応式

HRID 2197946 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[C:14]1([CH:21]=[CH:20][C:18]([OH:19])=[CH:17][CH:16]=1)[OH:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)[O:15][C:14]1[CH:21]=[CH:20][C:18]([OH:19])=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 330981-Chloro-3,5-dinitrobenzene

生成物 1

HCID 684558224-(3-Chloro-5-nitro-phenoxy)-phenol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

The product from Example 193a (1.00 g, 5.0 mmol), hydroquinone (0.50 g, 4.5 mmol) and K2CO3 (0.78 g, 5.6 mmol) in DMF (10 ml) was heated at 110° C. for 3.5 hours. The reaction mixture was cooled to room temperature, diluted with H2O and then extracted with EtOAc. The extract was washed with H2O and brine, dried over MgSO4, filtered and concentrated under vacuum giving the title compound. The residue was treated with i-Pr2O and insoluble material was filtered off. The filtrate was evaporated and purified by silica gel column chromatography eluting with 5:2 EtOAc/hexane to give the title product as pale yellow oil (0.51 g, 43%).

後処理

  1. extractionextracted with EtOAc
  2. washThe extract was washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-78700faa776a4ccd9963177adab44651
出典データセット
uspto-grants-2012_12
特許番号
US08338605B2

関連ノート

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