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

HRID 229241

反応式

HRID 229241 の反応式
[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

参加物

4

反応物 3

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

生成物 1

HCID 113102944-(3-Methoxy-3-oxopropyl)benzoic acid収率 84%

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-d08b68924eba4f69bfb540bae1614219
出典データセット
uspto-grants-2009_07
特許番号
US07560589B2

関連ノート

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