Formaldehyde → 3,7-Dimethyl-2-methylene-7-hydroxyoctanal

反応式

[CH3:1][CH:2]([CH2:10][CH:11]=[O:12])[CH2:3][CH2:4][CH2:5][C:6]([OH:9])([CH3:8])[CH3:7].C=O.[CH2:15](NCCCC)CCC.C(O)(=O)CCCCC>>[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][C:6]([CH3:8])([OH:9])[CH3:7])[C:10](=[CH2:15])[CH:11]=[O:12]

参加物

反応物 4

HCID 712Formaldehyde

HCID 7888Hydroxycitronellal2 回

HCID 8148Dibutylamine

HCID 8892Hexanoic Acid

生成物 1

HCID 866322753,7-Dimethyl-2-methylene-7-hydroxyoctanal収率 1,341.5%

反応条件

温度: 95 °C

実験手順

A 3 L four-necked flask equipped with a stirrer, a thermometer and a reflux condenser was charged with 1032 g (6.0 mol) of hydroxycitronellal, 520 g (6.4 mol) of a 37% by mass formaldehyde aqueous solution, 53 g (0.41 mol) of dibutyl amine and 10 g (0.09 mol) of hexanoic acid, and the contents in the flask were stirred while heating at 95° C. After the elapse of 40 min, it was confirmed that no hydroxycitronellal was present in the raw mixture, and then the mixture was cooled and separated into two layers. The thus separated organic layer was subjected to distillation treatment, thereby obtaining 1058 g (5.5 mol) of 3,7-dimethyl-2-methylene-7-hydroxyoctanal (purity as measured by gas chromatography: 95%) (yield based on theoretical amount: 92%).