Hydrochloric Acid → 4-(4-Isopropylphenyl)butanoic acid

HRID 1892092ノート

反応式

HRID 1892092 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].O.NN.[OH-].[K+].Cl>O>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 96145beta-(p-Cumoyl)propionic acid

生成物 1

HCID 3476744-(4-Isopropylphenyl)butanoic acid収率 58.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
127 °C

実験手順

A solution of compound 76 (0.5 g, 2.27 mmol) and 2 mL of 80% hydrazine hydrate was stirred at 45° C. for 1 hour. To the mixture, KOH (1 g, 17.8 mmol) was added and the reaction mixture was heated to 104-150° C. for 2 hours. After cooling to ambient temperature, the reaction mixture was diluted with 10 mL of water and acidified to pH 2 with aqueous HCl (1 M) and extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica-gel (2×15 cm, petroleum ether:ethyl acetate=8:1 elution) to give 275 mg of compound 77. MS m/z 207 (M+H)+.

後処理

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica-gel (2×15 cm, petroleum ether:ethyl acetate=8:1 elution)

出典と根拠

ORDレコード
ord-929ff638949f4427be462e707a860e8f
出典データセット
uspto-grants-2013_08
特許番号
US08507647B2

反応ノート

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