Methanol → 4-(3-Methoxy-3-oxopropyl)benzoic acid

HRID 1716092

반응식

HRID 1716092 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH3:19]O>>[CH3:19][O:13][C:12](=[O:14])[CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 8540543-(4-Carboxyphenyl)propionic Acid

생성물 1

HCID 113102944-(3-Methoxy-3-oxopropyl)benzoic acid수율 84%

실험 절차

To a suspension of 3-(4-carboxyphenyl)propionic acid (2.0 g, 10.1 mmol) in methanol (20 mL) was added thionyl chloride (38 μL, 0.50 mmol). The reaction mixture was stirred at room temperature for 16 h, and a clear solution was obtained. The solvent was removed under reduced pressure. The residue was taken up in ether (100 mL), washed with saturated aqueous NaHCO3 (2×50 mL) and water (50 mL). The combined NaHCO3 and water extract was acidified with concentrated HCl in an ice bath. The precipitated white solid was collected, washed with water and dried to yield 1.76 g (84%) of compound 166 as off-white solid. The material was used without further purification. mp 146-148° C. 1H NMR (400 MHz, CDCl3): δ 2.66 (t, J=7.7 Hz, 2H), 3.02 (t, J=7.7 Hz, 2H), 3.67 (s, 3H), 7.30 (d, J=8.3 Hz, 2H), 8.03 (d, J=8.1 Hz, 2H). LCMS (ES), m/z, 209 (M+H)+, 207 (M−H)−.

후처리

  1. customa clear solution was obtained
  2. customThe solvent was removed under reduced pressure
  3. washwashed with saturated aqueous NaHCO3 (2×50 mL) and water (50 mL)
  4. extractionThe combined NaHCO3 and water extract
  5. customwas acidified with concentrated HCl in an ice bath
  6. customThe precipitated white solid was collected
  7. washwashed with water
  8. customdried

출처 및 근거

ORD 기록
ord-460c4d127a5f4d93a6bf438272f51e77
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799828B2

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