Reaction #43902

Reaction equation

campholenic aldehyde

propionaldehyde

→

2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-en-1-al

Yield 80.6%

Conditions

Workup

1. 1
   OtherA 500 mL four-necked flask equipped with a stirrer
2. 2
   Temperaturecooled
3. 3
   Otherto remove amines
4. 4
   Otherseparating the mixture into two layers
5. 5
   WashThe thus separated organic layer was washed with water
6. 6
   Otherseparated into two layers

Procedure

A 500 mL four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel was charged with 171 g (0.98 mol) of campholenic aldehyde (purity: 88%), 3.8 g (0.045 mol) of piperidine and 2.8 g (0.046 mol) of acetic acid, and the contents in the flask were stirred while heating at 100° C. Then, 92 g (1.6 mol) of propionaldehyde was gradually dropped into the flask for 6 h, and the resultant mixture was aged for 1 h and then cooled. Thereafter, 3.2 g (0.053 mol) of acetic acid was added to the mixture to remove amines therefrom, thereby separating the mixture into two layers. The thus separated organic layer was washed with water and separated into two layers, thereby obtaining 279 g (0.79 mol) of 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-en-1-al (purity as measured by gas chromatography: 54.7%) (yield based on theoretical amount: 81%).

Source