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

HRID 2197946

반응식

HRID 2197946 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-78700faa776a4ccd9963177adab44651
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338605B2

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