Water → 3-(3,4-Dichlorophenyl)propan-1-ol

HRID 1515082ノート

反応式

HRID 1515082 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

5

反応物 3

HCID 962WaterHCID 6880273,4-Dichlorocinnamic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 190753133-(3,4-Dichlorophenyl)propan-1-ol収率 30%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

(2E)-3-(3,4-Dichlorophenyl)acrylic acid (800 mg, 3.69 mmol) was dissolved in tetrahydrofuran (80 mL), and the resulting solution was cooled to 0° C. Then, lithium aluminum hydride (280 mg, 7.38 mmol) was added thereto, and the temperature of the resulting mixture was raised to room temperature, and the mixture was stirred for 8 hours. Water was added to the reaction solution, and the organic matter was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30 (v/v)), whereby the objective title compound was obtained as a yellow oily substance (229 mg, yield: 30%).

後処理

  1. temperaturethe temperature of the resulting mixture was raised to room temperature
  2. extractionthe organic matter was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution, then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  7. customwas obtained
  8. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30 (v/v)), whereby the objective title compound
  9. customwas obtained as a yellow oily substance (229 mg, yield: 30%)

出典と根拠

ORDレコード
ord-e6c77b25cac34fdd8a568e09b63422a6
出典データセット
uspto-grants-2012_07
特許番号
US08222281B2

反応ノート

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