p-Methoxycinnamicaldehyde (p-cumaric aldehyde methyl ether) has been found in esdragon oil by Daufresne.1) Its constants are:

p   Methoxycinnamic aldehyde.

B. p. 170° (14 mm.); d0o 1,137. The semicarbazone melts at 222o the oxime at 154°.

The bisulphite addition product is not readily decomposed. When oxidized with potassium permanganate in acid solution, anisic acid results. Silver oxide oxidizes it top-methoxy cinnamic acid (m. p. 170°).

The aldehyde is identical with the artificial product prepared by Scholtz and Wiedemann.2) o-Methoxycinnamic aldehyde.

o-Methoxycinnamic aldehyde (o-cumaric aldehyde methyl ether) occurs occasionally as stearoptene in the oil of the CrWese cinnamon cassia1) and separates in solid form from the last fractions of cassia oil. M. p. 45 to 46°; b. p. abt. 295° with partial decomposition, 160 to 161° under 12 mm. pressure. It dyes the skin intensively yellow and is readily decomposible even away from air and light. Oxidation with permanganate converts it into methyl salicylic acid, m. p. 99°, which when boiled with hydriodic acid is converted into salicylic acid. With silver oxide it yields B-methylcumaric acid which melts at 182 to 183°. The oxime melts at 125 to 126°, the phenylhydrazone at 116 to 117°.

P Methoxycinnamic Aldehyde 159

1) Etude de /'essence d'estragon et de quelques d6rive's de l'estragol. These, Paris 1909; Compt. rend. 145 (1907), 875; Bull. des Sciences pharma-cologiques, January 1908, 11; Report of Schimmel & Co. April 1008, 49.

2) Berl. Berichte 36 (1903), 853.