Sodium Bicarbonate → Methyl 2-(4-formylphenyl)-2-methylpropanoate

HRID 2261786Notes

Reaction equation

HRID 2261786 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13]Br)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].C(=O)(O)[O-:17].[Na+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:17])=[CH:9][CH:8]=1)([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18423131Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoate

Product 1

HCID 25111210Methyl 2-(4-formylphenyl)-2-methylpropanoateYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To an ambient temperature solution of 2-(4-Bromomethyl-phenyl)-2-methyl-propionic acid methyl ester (275 mg, 1.01 mmol) in DMSO (8 mL) is added sodium bicarbonate (127 mg, 1.52 mmol). The reaction mixture is heated to 120° C. After 3 h, the reaction is concentrated and the residue is partitioned between EtOAc and NaHCO3. The aqueous layer is extracted with EtOAc and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 20% EtOAc/Hex) to yield the title compound (179 mg, 86%). 1H NMR (400 MHz, CDCl3) δ 10.00 (s, 1H), 7.85 (d, 2H, J=8.4 Hz), 7.50 (d, 2H, J=8.4 Hz), 3.67 (s, 3H), 1.61 (s, 6H).

Workup

  1. concentrationthe reaction is concentrated
  2. customthe residue is partitioned between EtOAc and NaHCO3
  3. extractionThe aqueous layer is extracted with EtOAc
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (0% to 20% EtOAc/Hex)

Sources & evidence

ORD record
ord-50d0bac183aa4610bfce511c1cbb9529
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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