p-Toluenesulfonic acid → Methyl 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylate

HRID 503440노트

반응식

HRID 503440 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[OH:8].[CH3:15]C1C=CC(S(O)(=O)=O)=CC=1>CO>[OH:1][C:2]1[CH:3]=[C:4]([C:9]2([C:12]([O:14][CH3:15])=[O:13])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[OH:8]

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 591293681-(3,4-Dihydroxyphenyl)cyclopropanecarboxylic acid

생성물 1

HCID 59129280Methyl 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylate수율 912.5%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

To a solution of 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylic acid (190 mg, 1.0 mmol) in MeOH (3 mL) was added 4-methylbenzenesulfonic acid (19 mg, 0.10 mmol). The mixture was heated at 80° C. overnight. The reaction mixture was concentrated in vacuo and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc twice and the combined organic layers were washed with sat. NaHCO3 and brine and dried over MgSO4. After the removal of solvent, the residue was dried in vacuo to yield methyl 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylate (190 mg, 91%) that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 6.76-6.71 (m, 2H), 6.66 (d, J=7.9 Hz, 1H), 3.56 (s, 3H), 1.50 (q, J=3.6 Hz, 2H), 1.08 (q, J=3.6 Hz, 2H).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. washthe combined organic layers were washed with sat. NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. customAfter the removal of solvent
  7. customthe residue was dried in vacuo

출처 및 근거

ORD 기록
ord-654068ede75845d98d1d9ffb1cb19b16
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776905B2

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