Water → 4-(2-Methylprop-1-en-1-yl)benzyl alcohol

HRID 457500

반응식

HRID 457500 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([CH3:20])=[CH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][CH:11]=1.O.[OH-].[Na+]>C(OCC)C>[CH3:7][C:8]([CH3:20])=[CH:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][OH:15])=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21989722Methyl 4-(2-methylprop-1-en-1-yl)-benzoate

생성물 1

HCID 691343894-(2-Methylprop-1-en-1-yl)benzyl alcohol수율 96.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

To a suspension of isopropyltriphenylphosphonium iodide (9.5 g) in tetrahydrofuran (90 mL) was added n-butyllithium (1.5 mol/L hexane solution, 15 mL) at 0° C., and the mixture was stirred for 15 minutes. To the reaction mixture was added a solution of methyl terephthalaldehydate (3.3 g) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethylacetate=3/1) and then by column chromatography on silica gel (eluent: dichloromethane/ethyl acetate=10/1)to give methyl 4-(2-methylprop-1-en-1-yl)benzoate (3.4 g). To a suspension of lithium aluminum hydride (0.68 g) in diethyl ether (120 mL) was added a solution of methyl 4-(2-methylprop-1-en-1-yl)benzoate (3.4 g) in diethyl ether (30 mL) at 0° C., and the mixture was heated under reflux for 50 minutes. After the reaction mixture was cooled to 0° C., water (0.69 mL), 15% aqueous sodium hydroxide solution (0.69 mL) and water (2 mL) were added, and the mixture was stirred at room temperature for 30 minutes. Insoluble materials were removed by filtrate, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1-2/1) to give 4-(2-methylprop-1-en-1-yl)benzyl alcohol (2.8 g).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 50 minutes
  3. customInsoluble materials were removed by filtrate
  4. customthe solvent of the filtrate was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1-2/1)

출처 및 근거

ORD 기록
ord-1c54035ad5d64c92b275a86061d9e95c
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189702B2

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