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ChemicalBook CAS DataBase List 4-(TERT-BUTYL)CINNAMIC ACID
1208-65-7

4-(TERT-BUTYL)CINNAMIC ACID synthesis

13synthesis methods
-

Yield: 85%

Reaction Conditions:

Stage #1:malonic acid;4-tert-Butylbenzaldehyde with piperidine;pyridine for 4 h;Heating / reflux;
Stage #2:hydrogenchloride in water; pH=3 at 0;

Steps:

1.1
Step 1 : Synthesis of (E)-3-[4-(t-butyl)phenyl]-2-acrylic acid; 4-(t-Butyl)benzaldehyde (0.5 mL, 3.0 mmol) was dissolved in pyridine(5.0 mL) and followed by adding malonic acid(470 mg, 4.5 mmol) thereto and adding dropwise piperidine (0.090 mL, 0.9 mmol). The reaction mixture was refluxed for 4 hours as confirming CO2 generation. After the completion of the reaction, the resultant mixture was acidified with 2N-HC1 at 00C and pH3 to yield a solid compound. The solid compound was filtered under reduced pressure and washed with H2O to obtain acidic compound (520 mg, 85%). EPO 1H-NMR (300MHz, CDCl3): δ 1.32 (s, 9H)3 6.43 (d, IH5 J = 16 Hz), 7.42 (d, 2H5 J = 8.61 Hz)5 7.50 (d, 2H5 J= 8.4 Hz)5 7.78 (d, IH, J= 16 Hz)

References:

AMOREPACIFIC CORPORATION WO2006/98554, 2006, A1 Location in patent:Page/Page column 42-43