Potassium Carbonate → p-Anisyl 4-formylcinnamate

HRID 2227495Notes

Reaction equation

HRID 2227495 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=[O:2].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([O:11][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)=[O:10])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 980772-Propenoic acid, 3-(4-formylphenyl)-

Product 1

HCID 86758303p-Anisyl 4-formylcinnamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 4-formylcinnamic acid (1.76 g), p-methoxybenzyl chloride (1.63 ml) and potassium carbonate (2.76 g) in 20 ml dimethylformamide was stirred at 80° C. for 7 hours, and then allowed to cool. The reaction mixture was extracted with ethyl acetate and washed with water. The combined organic layers were dried over magnesium sulfate. The drying agent was filtered off and the filtrate was evaporated under reduced pressure and dried to give p-anisyl 4formylcinnamate of interest (2.96 g, 100%) as a pale yellow solid.

Workup

  1. temperatureto cool
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe filtrate was evaporated under reduced pressure
  7. customdried

Sources & evidence

ORD record
ord-cbd305e009b9442cbf64f857e80aa513
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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