3-Methylbenzaldehyde → 5-(3-Methylphenyl)penta-2,4-dienoic acid

HRID 324390Notes

Reaction equation

HRID 324390 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O.[C:16]([O:21]C)(=[O:20])/[CH:17]=[CH:18]/[CH3:19]>C(O)(C)(C)C>[CH3:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:19][CH:18]=[CH:17][C:16]([OH:21])=[O:20])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 121053-MethylbenzaldehydeHCID 638132Methyl CrotonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 542427605-(3-Methylphenyl)penta-2,4-dienoic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of potassium tert-butoxide (68 g) and tert-butanol (130 ml) was treated dropwise with a mixture of 3-methylbenzaldehyde (33.8 g) and methyl crotonate (45 ml). The temperature of the reaction mixture rose to 65° C. during the addition and this was maintained for a further 3 hours. 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 diethyl ether. The organic phase was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by trituration with isohexane and filtration.

Workup

  1. additionThe temperature of the reaction mixture rose to 65° C. during the addition
  2. temperaturethis was maintained for a further 3 hours
  3. washwashed with diethyl ether
  4. extractionextracted with diethyl ether
  5. washThe organic phase was washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customPurification
  9. filtrationwas by trituration with isohexane and filtration

Sources & evidence

ORD record
ord-502e32c2ebd64212a9ee4e1a91f7090e
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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