methyl 4-methoxydihydrocinnamate

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Properties of substance:

methyl 3-(4-methoxyphenyl)propanoate

skc-file

Synonyms:

methyl 4-methoxydihydrocinnamate

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₁₁H₁₄O₃

Structural formula as text:

CH3OC6H4CH2CH2COOCH3

Synthesis 1:

Reference: Heffner, R. J., & Joullie, M. M. Synthetic Routes to Ninhydrins. Preparation of Ninhydrin, 5-Methoxyninhydrin, and 5-(Methylthio)Ninhydrin / Synthetic Communications. - 1991. - Vol. 21, No. 21 pp. 2248 [doi: 10.1080/00397919108055457]

CH₃OC₆H₄CH=CHCOOCH₃ + H₂ → CH₃OC₆H₄CH₂CH₂COOCH₃

To a solution of methyl 4-methoxycinnamate (8.00 g, 41.6 mmol) in ethanol (250 mL), and acetic acid (50 mL) at 25 °C, was added 10% palladium on activated carbon (1 g). The mixture was hydrogenated at 45 psi in a Parr apparatus. After one hour, the reaction mixture was filtered through Celite to remove the catalyst. The solids were washed with methanol (50 mL). The filtrate was evaporated under reduced pressure, and the resulting residue was azeotroped with toluene to remove residual acetic acid. Methyl 4-methoxydihydrocinnamate was obtained (8.0 g, 99% yield) as a solid. The crude compound was recrystallized from 2-propanol and water to afford the pure product, mp 37—39 °C, lit. mp 39 °C.

R_f 0.39 petroleum ether : ethyl acetate (90 : 10).

HRMS calcd. for C11H14O3 (M+): 194.094. Found: 194.094.

IR (CHCl3): 3008 (medium), 2970 (medium), 2875 (medium), 1735 (strong), 1617 (medium), 1590 (weak), 1510 (medium), 1440 (medium), 1370 (medium), 1305 (medium), 1245 (strong), 1130 (strong), 1110 (medium), 1040 (strong), 990 (weak), 950 (weak), 900 (weak), 860 (weak), 850 (weak), 830 (medium) cm^-1.

1H NMR (CDCl3): δ 2.59 (2H, m), 2.89 (2H, m), 3.66 (3H, s), 3.78 (3H, s), 6.83 (2H, m), 7.11 (2H, m).

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