methyl 4-methoxycinnamate

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Properties of substance:

methyl 4-methoxycinnamate

skc-file

Synonyms:

methyl (E)-3-(4-methoxyphenyl)acrylate

Group of substances:

organic

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

C₁₁H₁₂O₃

Structural formula as text:

CH3OC6H4CH=CHCOOCH3

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. 2247 [doi: 10.1080/00397919108055457]

(C₆H₅)₃P=CHCOOCH₃ + CH₃OC₆H₄CHO → CH₃OC₆H₄CH=CHCOOCH₃ + (C₆H₅)₃PO

To a solution of methyl(triphenylphosphoranylidene)acetate (25 g, 75.7 mmol) in tetrahydrofuran (68 mL) at 25 °C, was added p-anisaldehyde (6.78 g, 49.8 mmol). The solution was heated at reflux for 4 hours, and then evaporated under reduced pressure to afford an impure residue. This material was purified by column chromatography, eluting with petroleum ether : ethyl acetate (90 : 10) to afford methyl 4-methoxycinnamate (9.0 g, 94%). This solid was recrystallized from methanol to provide pure ester, mp 87—89 °C, lit. mp 89 °C.

R_f 0.32 petroleum ether : ethyl acetate (90 : 10).

HRMS calcd. for C11H12O3 (M+H): 192.079. Found: 192.082.

IR (CHCl3): 3020 (weak), 2970 (weak), 2855 (weak), 1710 (strong), 1640 (medium), 1610 (medium), 1580 (medium), 1512 (medium), 1464 (weak), 1440 (medium), 1320 (medium), 1408 (medium), 1390 (medium), 1260 (strong), 1170 (strong), 1110 (weak), 1034 (medium), 985 (medium), 937 (weak), 860 (weak), 850 (weak), 830 (medium) cm^-1.

1H NMR (CDCl3): δ 3.79 (3H, s), 3.83 (3H, s), 6.31 (1H, d, J = 15.9 Hz), 6.90 (2H, d, J = 8.8 Hz), 7.47 (2H, d, J = 8.8 Hz), 7.65 (1H, d, J = 15.9 Hz).

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