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

HRID 229241Notes

Reaction equation

HRID 229241 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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)−.

Workup

  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

Sources & evidence

ORD record
ord-d08b68924eba4f69bfb540bae1614219
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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