Hydrochloric Acid → Methyl 4-(2-oxoethyl)benzoate

HRID 2261788Notes

Reaction equation

HRID 2261788 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][O:12]C)=[CH:6][CH:5]=1.Cl>C1COCC1.O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54136641Methyl 4-(2-methoxyethenyl)benzoate

Product 1

HCID 13844675Methyl 4-(2-oxoethyl)benzoateYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 4-(2-Methoxy-vinyl)-benzoic acid methyl ester (930 mg, 4.84 mmol) in THF (50 mL) is added conc. HCl (7 mL) dropwise. After 2 h, the reaction is diluted with water and the pH is adjusted to 7. The aqueous layer is extracted with Et2O (2×200 mL). The combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 30% EtOAC/Hex) to yield the title compound (613 mg, 71%). 1H NMR (400 MHz, CDCl3) δ 9.77 (t, 1H, J=2.2 Hz), 8.04 (d, 2H, J=8.4 Hz), 7.30 (d, 2H, J=8.8 Hz), 3.92 (s, 3H), 3.77 (d, 2H, J=2.2 Hz).

Workup

  1. extractionThe aqueous layer is extracted with Et2O (2×200 mL)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (0% to 30% EtOAC/Hex)

Sources & evidence

ORD record
ord-095c00008d1441bba8000b0c5020c6ee
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…