4-Isopropoxybenzaldehyde → 1-Methoxy-2-(4-[isopropoxy]phenyl)ethene

HRID 275222

반응식

HRID 275222 반응식
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:24]([O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)([CH3:26])[CH3:25].C(=O)([O-])O.[Na+]>COC(C)(C)C>[CH3:2][O:3][CH:4]=[CH:32][C:31]1[CH:34]=[CH:35][C:28]([O:27][CH:24]([CH3:26])[CH3:25])=[CH:29][CH:30]=1

참가 물질

5

반응물 3

HCID 2500774-IsopropoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 2723798Methoxymethyl-triphenylphosphonium chloride

생성물 1

HCID 540504781-Methoxy-2-(4-[isopropoxy]phenyl)ethene수율 93.7%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매2회

반응 조건

온도
0 °C

실험 절차

A suspension of 140 g of methoxymethyl-triphenylphosphonium chloride in 400 ml of tert.-butyl methyl ether is treated with 45 g of potassium tert.-butylate within 5 minutes at 0° C. while gassing with nitrogen and the mixture is stirred for a further 10 minutes. Then, a solution of 41 g of 4-(isopropyloxy)-benzaldehyde in 100 ml of tert.-butyl methyl ether is added dropwise at 0° C. within 30 minutes. The reaction mixture is stirred at room temperature for a further 16 hours and then poured into 750 ml of 0.8N sodium hydrogen carbonate solution. The aqueous phase is separated and back-extracted with diethyl ether. The organic phase is washed neutral with water, dried over magnesium sulphate and concentrated. The residue is suspended in 800 ml of hexane. After cooling to 0° C. the triphenylphosphine oxide is filtered off and the filtrate is concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 9:1) gives 45 g of pure 1-methoxy-2-(4-[isopropoxy]phenyl)ethene.

후처리

  1. stirringThe reaction mixture is stirred at room temperature for a further 16 hours
  2. customThe aqueous phase is separated
  3. extractionback-extracted with diethyl ether
  4. washThe organic phase is washed neutral with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. filtrationis filtered off
  8. concentrationthe filtrate is concentrated

출처 및 근거

ORD 기록
ord-f7e197db34504310b76a939086711b95
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393458

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