Methanol → 4-(2-Methoxy-2-oxoethyl)benzoic acid

HRID 2100131Notes

Reaction equation

HRID 2100131 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:2][C:1](=[O:3])[CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2200054-(Carboxymethyl)benzoic Acid

Product 1

HCID 138161444-(2-Methoxy-2-oxoethyl)benzoic acidYield 88%

Procedure

To a suspension of 4-(carboxymethyl)benzoic acid (2.43 g, 13.5 mmol) in methanol (30 mL) was added thionyl chloride (50 μL, 0.67 mmol). The reaction mixture was stirred at room temperature for 5.5 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 (30 mL). The combined NaHCO3 and water extract was acidified with concentrated HCl in an ice bath. The white precipitation was collected and washed with water, dried to yield 2.30 g (88%) compound 150 as white solid. The material was used without further purification. mp 134-136° C. 1H NMR (400 MHz, CDCl3): δ 3.71 (s, 5H), 7.40 (d, J=8.2 Hz, 2H), 8.07 (d, J=8.2 Hz, 2H). LCMS (ESI), m/z, 193 (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 (30 mL)
  4. extractionThe combined NaHCO3 and water extract
  5. customwas acidified with concentrated HCl in an ice bath
  6. customThe white precipitation
  7. customwas collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-b3e9532e6fd341d297b66fb3962435ea
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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