2-Methylundecanal
- (RS )-2- methylundecanal
- (R )-2- methylundecanal
- (S )-2- methylundecanal
- Rac-2- methylundecanal
- (± )-2- methylundecanal
- ( )-2- methylundecanal
- (-) -2- methylundecanal
- Methylnonylacetaldehyd
- Aldehyde C12 MNA
Colorless liquid with a fruity odor
Liquid
0.83 g · cm -3
171 ° C
Soluble in alcohol, insoluble in water
1.432 (20 ° C)
Template: Infobox chemical / molecular formula search available
2- methylundecanal is a chemical compound that became known as the first fully synthetic fragrance Chanel N ° 5, 1921, in the top note. It occurs naturally in the skin of the kumquat fruit. The connection smells herbaceous, to Orange and amber. In high dilution it smells of honey and nuts. The compound is a colorless to slightly yellowish liquid in organic solvents such as ethers and ethanol is readily soluble. It is used as a fragrance in soaps, cleaning agents and perfumes.
Chemical extraction and properties
2- methylundecanal belongs to the group of aliphatic aldehydes.
The compound was first synthesized by Georges Darzens in 1904 from 2- undecanone ( methyl nonyl ketone ) and chloroacetic acid using the Darzens reaction. The synthesis route is in use even today.
Industrial two synthesis paths are taken. The synthesis takes place via the reaction of 2- alkyl chloroacetate under undecanone and saponification and decarboxylation.
The second method starts with the conversion of undecanal with formaldehyde in the presence of a base followed by hydrogenation. The starting material is undecanal of 1 -decene hydroformylation about accessible.
Stereoisomerism
2- methylundecanal contains a stereocenter, so there are two enantiomers, (R )-2- methylundecanal (top) and (S )-2- methylundecanal ( below):
The enantiomers are selectively produced by Enders reagent ( SAMP / RAMP method).