p-Toluenesulfonic acid → Methyl 1-phenylcyclopropane-1-carboxylate

HRID 503278

반응식

HRID 503278 반응식
[C:1]1([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13]C1C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>CO>[C:1]1([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 802061-Phenylcyclopropanecarboxylic acid

생성물 1

HCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate수율 147.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 1-phenylcyclopropanecarboxylic acid (25 g, 0.15 mol) in CH3OH (200 mL) was added TsOH (3 g, 0.1 mol) at room temperature. The mixture was refluxed overnight. The solvent was evaporated under reduced pressure to give crude product, which was dissolved into EtOAc. The EtOAc layer washed with aq. sat. NaHCO3. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to give methyl 1-phenylcyclopropanecarboxylate (26 g, 96%), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 7.37-7.26 (m, 5H), 3.63 (s, 3H), 1.63-1.60 (m, 2H), 1.22-1.19 (m, 2H).

후처리

  1. temperatureThe mixture was refluxed overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customto give crude product, which
  4. washThe EtOAc layer washed with aq. sat. NaHCO3
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-983aea54acea40789ee87e0e1c273d96
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776905B2

연결된 노트

불러오는 중…