Methanol → Methyl 2-(4-mercaptophenyl)acetate

HRID 424797

반응식

HRID 424797 반응식
[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

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 33905114-Mercaptophenylacetic acid

생성물 1

HCID 14033178Methyl 2-(4-mercaptophenyl)acetate수율 68%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-92ab3ad5b44f420e9b75574f703cfd83
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106077B2

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