Benzaldehyde → Diethyl (phenylmethylene)malonate

HRID 1185454Notes

Reaction equation

HRID 1185454 reaction equation
CC[O-].[Na+].[CH:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:13]([O:15][C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:14].Cl>C(O)C>[CH2:13]([O:15][C:16](=[O:23])[C:17](=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:14]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxide

Product 1

HCID 94751Diethyl (phenylmethylene)malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 12.8 g sodium ethylate in 140 ml of ethanol, 10.0 g of benzaldehyde and 17.4 g of Malonic acid diethyl ester dissolved in 35 ml ethanol was added drop-wise over 1 h at 50° C. Then, the reaction mixture was heated to reflux for 12 h. After cooling to RT half of the solvent was evaporated under reduced pressure and diluted with 200 ml of water. The remaining reaction mixture was acidified to pH 1 by addition of concentrated hydrochloric acid and then extracted with ethyl acetate. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was pure enough for the next reaction step.

Workup

  1. additionwas added drop-wise over 1 h at 50° C
  2. temperatureThen, the reaction mixture was heated
  3. temperatureto reflux for 12 h
  4. customwas evaporated under reduced pressure
  5. additiondiluted with 200 ml of water
  6. customThe remaining reaction mixture
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase was dried over MgSO4
  9. customthe solvents were removed under reduced pressure
  10. customThe crude product was pure enough for the next reaction step

Sources & evidence

ORD record
ord-5a541300240f4b6ea5f6e68bc37f3c37
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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