Methanol → Methyl 3-formylbenzoate

HRID 2307691Notes

Reaction equation

HRID 2307691 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])=[O:2].CO.[C:14]([O-])([O-])=O.[Cs+].[Cs+].IC>O>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:8][CH3:14])=[O:7])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 120773-Carboxybenzaldehyde

Product 1

HCID 639145Methyl 3-formylbenzoateYield 164.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-Formylbenzoic acid (3.11 g, 20.7 mmol, Aldrich) in 10:1 methanol:water (110 mL) was treated with Cs2CO3 (3.11 g, 10.4 mmol). After stirring 18 hours, the solvent was evaporated under reduced pressure and the residue was dried under reduced pressure at 60° C. The residue was suspended in DMF (40 mL) and treated with iodomethane (2.58 mL, 41.4 mmol). After stirring at ambient temperature 2 hours, the mixture was poured into water and extracted with diethyl ether. The ether extracts were combined, washed with water, saturated NaHCO3, dried (MgSO4), filtered and the filtrate concentrated under reduced pressure to provide the title compound as a white solid (2.81 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was dried under reduced pressure at 60° C
  3. stirringAfter stirring at ambient temperature 2 hours
  4. extractionextracted with diethyl ether
  5. washwashed with water, saturated NaHCO3
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-0ee1abb37a5e406e812c25493f910ce1
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

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