3-Methoxybenzaldehyde → Methyl 5-(3-methoxyphenyl)penta-2,4-dienoate

HRID 324405Notes

Reaction equation

HRID 324405 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O.[C:17]([O:22][CH3:23])(=[O:21])/[CH:18]=[CH:19]/[CH3:20]>C(O)(C)(C)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:20][CH:19]=[CH:18][C:17]([O:22][CH3:23])=[O:21])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 638132Methyl CrotonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 71366468Methyl 5-(3-methoxyphenyl)penta-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of potassium tert-butoxide (52 g) and tert-butanol (170 ml) was treated dropwise with a mixture of 3-methoxybenzaldehyde (30 g) and methyl crotonate (35 ml). The temperature of the reaction mixture rose to 80° C. during the addition and was then maintained for a further 3 hours at 65° C. The reaction mixture was cooled to room temperature, poured into ice/water and washed with diethyl ether. The aqueous phase was acidified with concentrated HCl and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and evaporated under reduced pressure to yield an orange oil. Yield 53.2 g. Used directly in the next step.

Workup

  1. additionThe temperature of the reaction mixture rose to 80° C. during the addition
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customto yield an orange oil

Sources & evidence

ORD record
ord-c6f71d167710414abbaea39895314fd2
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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