1-(p-Tolyl)cyclopropanecarboxylic acid → Methyl 1-(p-tolyl)cyclopropanecarboxylate

HRID 332679노트

반응식

HRID 332679 반응식
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.O.[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([C:7]2([C:10]([O:12][CH3:15])=[O:11])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 986391-(p-Tolyl)cyclopropanecarboxylic acidHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 57443305Methyl 1-(p-tolyl)cyclopropanecarboxylate수율 969.3%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
75 °C

실험 절차

To a stirred solution of 1-(p-tolyl)cyclopropanecarboxylic acid (6 g, 34.05 mmol) in methanol (48 mL), was added para-toluenesulphonic acid monohydrate (0.648 g, 3.405 mmol). The reaction was stirred at 75° C. for 16 hours. The mixture was concentrated under reduced pressure, and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated aqueous sodium bicarbonate solution (×2), brine and dried (magnesium sulfate), filtered, and concentrated under reduced pressure to afford the title compound as an orange oil (6.279 g, 97%). The material was used directly in the next step with no further purification.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (×2), brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fe34e0c1a34e4020bb1a957d88d61f8d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877774B2

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