2,6,10-Trimethyl-dodecan-1-al and 2,6,10-trimethyl-dodeca-4,8-di

Details 2,6,10-Trimethyl-dodecan-1-al and 2,6,10-trimethyl-dodeca-4,8-di 2,6,10-Trimethyl-dodecan-1-al and 2,6,10-trimethyl-dodeca-4,8-di

1975-08-01

1977-01-04

Thomas, Jr., James O.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

252522, 426534, C07C 4702

Patent

active

040013367

ABSTRACT:
2,6,10-Trimethyl-dodecan-1-al and its 4,8-diene and processes for their manufacture. The new compounds are manufactured by vinylation or ethynylation and subsequent partial hydrogenation of 2-methyl-butan-1-al, reaction of the resulting 4-methyl-hex-1-en-3-ol with a propenyl ether in the presence of an acid catalyst at elevated temperatures, or reaction of the resulting 4-methyl-hex-1-en-3-ol with an .alpha.-formyl-propionic acid ester at elevated temperatures, subsequent vinylation of ethynylation and partial hydrogenation of the resulting 2,6-dimethyl-oct-4-en-1-al, renewed reaction with a propenyl ether or an .alpha.-formyl-propionic acid ester and -- if desired -- catalytic hydrogenation of the resulting 2,6,10-trimethyl-dodeca-4,8-dien-1-al. The organoleptic properties of the new compounds greatly resemble those of the natural scents and aromas of oranges, namely .alpha.- and .beta.-sinensal. They have the advantage over the sinensals of being more stable to acid and alkali, and are therefore particularly suitable for flavoring, eg., carbonated beverages, or for perfuming alkaline products. In addition they are industrially substantially simpler to produce than are the sinensals.

REFERENCES:
patent: 2815386 (1957-12-01), Surmatis
Chang, "Chemical Abstracts" vol. 59 (1963) 3869-3874 especially 3871e.
Schudel et al. "Chemical Abstracts" vol. 59 (1963) 2757-2758, esp. 2758.

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