Veratraldehyde → Ethyl 3-(3,4-dimethoxyphenyl)prop-2-enoate

HRID 1488942Notes

Reaction equation

HRID 1488942 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH2:8]P(OCC)(OCC)=O)=[O:7].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH:22]=O>O1CCCC1>[CH2:4]([O:5][C:6](=[O:7])[CH:8]=[CH:22][C:21]1[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:19]([O:18][CH3:17])[CH:20]=1)[CH3:3]

Participants

5

Reactant 3

HCID 8419VeratraldehydeHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

Product 1

HCID 2794876Ethyl 3-(3,4-dimethoxyphenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

16.5 g (0.55 mol) of sodium hydride (80%) are stirred in 500 ml of tetrahydrofuran and 123.3 g (0.55 mol) of phosphonoacetic acid triethyl ester are added dropwise to give a clear solution. Then over 15 minutes a solution of 83.1 g (0.50 mol) of 3,4-dimethoxybenzaldehyde in 200 ml of tetrahydrofuran are added. The mixture is then stirred under reflux for 30 minutes. After cooling, the clear solution is separated from the insoluble material which is dissolved in 500 ml of water and extracted twice with 250 ml of toluene. The tetrahydrofuran solution is evaporated to dryness and the residue is dissolved in the toluene extract. This solution is washed three times with water, dried and the solvent evaporated.

Workup

  1. customto give a clear solution
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. customthe clear solution is separated from the insoluble material which
  5. dissolutionis dissolved in 500 ml of water
  6. extractionextracted twice with 250 ml of toluene
  7. customThe tetrahydrofuran solution is evaporated to dryness
  8. dissolutionthe residue is dissolved in the toluene
  9. extractionextract
  10. washThis solution is washed three times with water
  11. customdried
  12. customthe solvent evaporated

Sources & evidence

ORD record
ord-b859bb0b81b84c2482a9f18ff6f9f215
Source dataset
uspto-grants-1997_10
Patent number
US05677303

Reaction notes

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