2-фенилпропиональдегид

Химические свойства

2-PHENYLPROPIONALDEHYDE identified in dried mushroom, is a colorless liquid with a green hyacinth odor. Hydratropaldehyde can be hydrogenated to hydratropic alcohol, which is also used to a limited extent by reaction of p-ethylbenzyl chloride and isobutyric aldehyde in the presence of catalysts. The product is used in perfumes for, for example, household products.

Вхождение

Reported found in microbially fermented tea and some varieties of mushrooms.

Использование

2-Phenylpropionaldehyde is a precursor in the synthesis of N,N,β-Trimethyl-phenethylamine Hydrochloride (T796625).

Подготовка

By alkaline condensation of acetophenone and ethyl chloroacetate; also by distillation of methylphenyl ethylene glycol in 91% yields (under atmospheric pressure).

Методы производства

The most important synthetic route to 2-phenylpropionaldehyde is the rhodiumcatalyzed hydroformylation of styrene. The catalyst [HCo(CO)4] is unsuitable in this process because it favors the hydrogenation of styrene. The use of chiral rhodium complexes leads to the formation of optically active aldehydes when prochiral olefins, such as styrene, are used. Asymmetric hydroformylation, however, has so far found only small industrial application because of insufficient purity of the enantiomers. Other synthetic methods are the gas-phase oxidation of a-methylstyrene on Cu, Bi–Mo– P–SiO2, or Pd salt catalysts, the rearrangement of epoxidized a-methylstyrene, and the dehydrogenation of 2-phenyl-1-propanol on Ag catalysts at reaction temperatures of ca. 600 ℃.

Общее описание

2-Phenylpropionaldehyde is used in perfumes for its green hyacinth odor.

Торговое название

Floralozone (IFF), Florazon (Symrise).

Профиль безопасности

: Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Методы очистки

It may contain up to 15% of acetophenone. Purify it via the bisulfite addition compound [Lodge & Heathcock J Am Chem Soc 109 3353 1987] and see Chapter 2 for preparation and decomposition of bisulfite adducts. [Beilstein 7 IV 695.]