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

HRID 457500

反応式

HRID 457500 の反応式
[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

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21989722Methyl 4-(2-methylprop-1-en-1-yl)-benzoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1c54035ad5d64c92b275a86061d9e95c
出典データセット
uspto-grants-2007_03
特許番号
US07189702B2

関連ノート

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