4-Hydroxybenzaldehyde → 4-Isopropoxybenzaldehyde

HRID 351817

반응식

HRID 351817 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH:17]([CH3:19])[CH3:18]>CN(C=O)C>[CH:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:19])[CH3:18]

참가 물질

5

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 6362Isopropyl iodideHCID 11430Potassium Carbonate

생성물 1

HCID 2500774-Isopropoxybenzaldehyde수율 77.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2 g (16.38 mmol) of 4-hydroxybenzaldehyde in 100 mL of DMF, 2.72 g (19.69 mmol) of K2CO3, 2.74 g (16.52 mmol) of KI and 3.94 mL (39.38 mmol) of 2-iodopropane was added under argon. The mixture was stirred at 80° C. overnight, concentrated and the residue obtained was partitioned between CHCl3 and H2O. The phases were separated, the aqueous phase was extracted with CHCl3 and the combined organic phases were dried over MgSO4 and concentrated. The crude product obtained was purified by chromatography on silica gel using EtOAc/hexane mixtures of increasing polarity as eluent, to give 2.08 g of the title compound of the example as an oil (77% yield).

후처리

  1. concentrationconcentrated
  2. customthe residue obtained
  3. customwas partitioned between CHCl3 and H2O
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with CHCl3
  6. dry with materialthe combined organic phases were dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product obtained
  9. customwas purified by chromatography on silica gel
  10. temperatureof increasing polarity as eluent

출처 및 근거

ORD 기록
ord-894b4acbbcc04531b679f4df06420873
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743816B2

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