|
|Section2= |Section3= |Section4= }} 2-Methylundecanal is an organic compound that is found naturally in kumquat peel oil. This compound smells herbaceous, orange, and ambergris-like.〔(Molecule of the Month: Chanel No 5 and 2-methylundecanal )〕 At high dilution it has a flavor similar to honey and nuts.〔 It is a colorless or pale yellow liquid that is soluble in organic solvents such as ether and ethanol. It is used as a fragrance component in soaps, detergents, and perfumes. == Preparation == The first synthesis of 2-methylundecanal was recorded by Georges Darzens in 1904 from methyl nonyl ketone and ethyl chloroacetate. This method of synthesis can be used to produce a variety of aldehydes and became known as the Darzens reaction and is still used today. 2-Methylundecanal is synthesized in industry by two main routes. The first route, like Darzens, involves converting methyl nonyl ketone to its glycidate by allowing it to react with alkyl chloroacetate. The glycidate then undergoes saponification followed by decarboxylation. :CH3(CH2)8C(O)CH3 + ClCH2CO2CH3 → CH3(CH2)8CH(CH3)OCH(CO2R) + HCl :CH3(CH2)8CCH3OCCO2CH3 + H2O → CH3(CH2)8CH(CH3)CHO + CO2 + ROH The second method for the synthesis of 2-methylundecanal begins with the conversion of undecanal to 2-methyleneundecanal by allowing it to react with formaldehyde in the presence of base. The 2-methyleneundecanal is then hydrogenated to give 2-methylundecanal. The required undecanal is generated from 1-decene by hydroformylation. The resulting solution is over 50% 2-methyleneundecanal. The double bond of this compound is hydrogenated and the resulting 2-methylundecanal is separated from the by-products using fractional distillation.〔 :CH3(CH2)7CH2=CH2 + H2 + CO → CH3(CH2)10CHO :CH3(CH2)10CHO + HCHO → CH3(CH2)8C(CH2)CHO + H2O :CH3(CH2)8C(CH2)CHO + H2 → CH3(CH2)8CH(CH3)CHO 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「2-Methylundecanal」の詳細全文を読む スポンサード リンク
|