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

HRID 503440ノート

反応式

HRID 503440 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-654068ede75845d98d1d9ffb1cb19b16
出典データセット
uspto-grants-2010_08
特許番号
US07776905B2

反応ノート

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