3-(4-Carboethoxy)phenyl propanal Chemical Properties

Boiling point:

312.4±25.0 °C(Predicted)

Density 

1.082±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

CAS DataBase Reference

151864-81-2(CAS DataBase Reference)

3-(4-Carboethoxy)phenyl propanal Usage And Synthesis

Synthesis

Ethyl 4-iodobenzoate (200 g, 0.725 mol) and acryl alcohol (63 g, 1.087 mol) were added with stirring to a DMF (600) containing sodium bicarbonate (152 g, 1.812 mol), tetrabutylammonium bromide (117 g, 0.362 mol) and palladium(II) acetate (3.2 g, 0.014 mol) in a 600 mL) in suspension. The reaction mixture was heated to 75-80 °C and kept at this temperature for 3-3.5 h. The reaction was subsequently cooled to 40-50 °C. Under vigorous stirring, toluene (1 L) was added to the reaction mixture and stirring was continued for 15 minutes. The mixture was filtered through a diatomaceous earth pad and the diatomaceous earth pad was washed with toluene (2 x 200 mL). The filtrate and washings were combined, washed with water (3 x 1 L) and then evaporated to constant weight at 30-40 °C and 10 mmHg. 147.5 g (98.8% yield, 84% HPLC purity) of ethyl 4-(3-oxopropyl)benzoate crude product was obtained as a dark brown oil, which could be used in the next step without further purification.1H NMR (DMSO-d6): δ 1.38 (t, 3H), 2.81 (t, 2H), 3.03 (t, 2H), 4.39 (q, 2H) , 7.27 (d, 2H), 7.98 (d, 2H), 9.81 (s, 1H).

References

[1] Tetrahedron Letters, 1999, vol. 40, # 21, p. 4023 - 4026
[2] Patent: US2005/49296, 2005, A1. Location in patent: Page/Page column 7-8
[3] Organic Letters, 2009, vol. 11, # 22, p. 5342 - 5345
[4] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 6, p. 941 - 946
[5] Patent: WO2006/63863, 2006, A1. Location in patent: Page/Page column 43-44; 1/2

3-(4-Carboethoxy)phenyl propanal(151864-81-2)Related Product Information

• Phenyl salicylate
• Stearoylbenzoylmethane
• Ethylparaben
• Diphenyl ether
• 2-Ethoxyethanol
• 4-Methylbenzenesulfonhydrazide
• Ethanol
• Ethyl acetate
• Benzoyl hydrazine
• Benzoyl cyanide
• Benzoyl peroxide
• Propionaldehyde
• Tris(trimethylsilyl)phosphate
• Trinexapac-ethyl
• Dimethyl succinate
• ISOXADIFEN-ETHYL
• PHENYL VALERATE
• Methyl acrylate