Ammonium Acetate → Methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate

HRID 1691523ノート

反応式

HRID 1691523 の反応式
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH:12]2[C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1)(=O)C.C([O-])(=O)C.[NH4+]>CO.O>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:13][CH:12]2[C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:10]=1

参加物

5

反応物 2

HCID 517165Ammonium AcetateHCID 59364054Methyl 2-[4-(acetyloxy)phenyl]cyclopropane-1-carboxylate

生成物 1

HCID 59364069Methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate収率 96%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Methyl 2-[4-(acetyloxy)phenyl]cyclopropanecarboxylate (2.26 g, 9.65 mmol) was dissolved in a mixed solvent of methanol (80 mL) and water (20 mL), and ammonium acetate (5.95 g, 77.2 mmol) was added. The mixture was stirred at room temperature for 10 hr and further stirred at 60° C. for 8 hr. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60) to give the title compound (1.78 g, yield 96%) as colorless crystals.

後処理

  1. additionwas added
  2. stirringfurther stirred at 60° C. for 8 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60)

出典と根拠

ORDレコード
ord-673af29b4c074b67b40a7c6db9c941bc
出典データセット
uspto-grants-2012_04
特許番号
US08153694B2

反応ノート

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