4-Formylbenzoic acid → Methyl 4-Formylbenzoate

HRID 53567Notes

Reaction equation

HRID 53567 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH3:12][Si](C=[N+]=[N-])(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:12][O:2][C:1](=[O:3])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 120884-Formylbenzoic acidHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium Bicarbonate

Product 1

HCID 15294Methyl 4-Formylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 9.6 g (63.6 mmol) of 4-carboxybenzaldehyde (Aldrich Chemical Co.) in 100 mL of CH2Cl2 at 0° C. was added excess trimethylsilyldiazomethane and the resulting mixture was allowed to stir at 0° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated to give 4.3 g of the ester 167 as an oil. 1H NMR consistent with the product.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5d2cea90eaed40cca443da22d2d9ed59
Source dataset
uspto-grants-1997_04
Patent number
US05620971

Reaction notes

Loading…