3-Hydroxybenzaldehyde → 2-(3-Formyl-phenoxy)-4-methyl-benzonitrile

HRID 1243728

반응식

HRID 1243728 반응식
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+]([O-])=O)[CH:3]=1.[OH:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH:17]([C:16]1[CH:15]=[C:14]([CH:21]=[CH:20][CH:19]=1)[O:13][C:4]1[CH:3]=[C:2]([CH3:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])=[O:18]

참가 물질

6

반응물 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 10796Cesium carbonateHCID 962352-Nitro-4-toluonitrile

생성물 1

HCID 219304102-(3-Formyl-phenoxy)-4-methyl-benzonitrile수율 36%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Methyl-2-nitrobenzonitrile (0.50 g, 3.1 mmol), 3-hydroxybenzaldehyde (0.38 g, 3.1 mmol) and cesium carbonate (1.00 g, 3.1 mmol) were heated with stirring in dry DMF (5 mL) at 80° C. for 28 h. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with 0.1N sodium hydroxide solution (3×), water (1×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 2-(3-formyl-phenoxy)-4-methyl-benzonitrile (0.26 g, 36%) as a brown resin, and was carried forward without further purification.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with 0.1N sodium hydroxide solution (3×), water (1×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-2376f183c6134766b7bf9e0bdc354ed6
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119122B2

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