Methanol → Methyl 2-(4-mercaptophenyl)acetate

HRID 424797

反応式

HRID 424797 の反応式
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([SH:1])=[CH:7][CH:6]=1

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 33905114-Mercaptophenylacetic acid

生成物 1

HCID 14033178Methyl 2-(4-mercaptophenyl)acetate収率 68%

実験手順

To an ambient temperature solution of 4-mercaptophenylacetic acid (5.0 g, 29.72 mmol) in MeOH (250 mL) is added sulfuric acid (1.25 mL). The reaction is stirred at room temperature overnight. The reaction mixture is concentrated and the residue is partitioned between Et2O and water. The aqueous layer is extracted with Et2O and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed eluting with 0% to 30% EtOAC/Hexane to yield the title compound (3.69 g, 68%). 1H NMR (400 MHz, CDCl3) δ 7.21 (d, 2H, J=7.9 Hz), 7.12 (d, 2H, J=8.4 Hz), 3.66 (s, 3H), 3.54 (s, 2H).

後処理

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is partitioned between Et2O and water
  3. extractionThe aqueous layer is extracted with Et2O
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed
  9. washeluting with 0% to 30% EtOAC/Hexane

出典と根拠

ORDレコード
ord-92ab3ad5b44f420e9b75574f703cfd83
出典データセット
uspto-grants-2012_01
特許番号
US08106077B2

関連ノート

読み込み中…