Dimethyl Succinate → (E)-3-Methoxycarbonyl-4-(3-methylphenyl)-3-butenoic acid

HRID 1590170Notes

Reaction equation

HRID 1590170 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=O.[C:13]([O:21]C)(=[O:20])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]>CO>[CH3:19][O:18][C:16](/[C:15](=[CH:8]/[C:7]1[CH:10]=[CH:11][CH:12]=[C:5]([CH3:4])[CH:6]=1)/[CH2:14][C:13]([OH:21])=[O:20])=[O:17]

Participants

5

Reactant 3

HCID 7820Dimethyl SuccinateHCID 121053-MethylbenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 19769729(E)-3-Methoxycarbonyl-4-(3-methylphenyl)-3-butenoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide (1.4 g) in methanol (20 ml}was added a mixture of 3-methylbenzaldehyde (2.4 g) and dimethyl succinate (3.5 g) and the mixture was refluxed for 3 hours. After the reaction mixture was concentrated in vacuo, water was added to the resulting residue and the mixture was washed with diethyl ether. The aqueous layer was acidified with hydrochloric acid and extracted with diethyl ether. The organic layer was washed with brine and dried over MgSO4. The solvent was evaporated under reduced pressure to give 3.8 g of

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. concentrationAfter the reaction mixture was concentrated in vacuo, water
  3. additionwas added to the resulting residue
  4. washthe mixture was washed with diethyl ether
  5. extractionextracted with diethyl ether
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated under reduced pressure
  9. customto give 3.8 g of

Sources & evidence

ORD record
ord-142856271e9345cdb66ba170303516a2
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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