Propanal → 2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal

HRID 15620

反応式

HRID 15620 の反応式
[CH3:1][C:2]1[C:6]([CH3:8])([CH3:7])[CH:5]([CH2:9][CH:10]=O)[CH2:4][CH:3]=1.[CH:12](=[O:15])[CH2:13][CH3:14]>C(NCCCC)CCC.C(O)(=O)CCCCC.C(O)(=O)C>[CH3:14][C:13](=[CH:10][CH2:9][CH:5]1[CH2:4][CH:3]=[C:2]([CH3:1])[C:6]1([CH3:7])[CH3:8])[CH:12]=[O:15]

参加物

6

反応物 2

HCID 527PropanalHCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

生成物 1

HCID 30175572-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal収率 93.9%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 8148Dibutylamine触媒HCID 8892Hexanoic Acid触媒

反応条件

温度
100 °C

実験手順

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%), 5.8 g (0.045 mol) of dibutyl amine and 5.3 g (0.046 mol) of hexanoic acid, and the contents in the flask were stirred while heating at 100° C. Then, 91 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 further separated into two layers, thereby obtaining 280 g (0.92 mol) of 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-en-1-al (purity as measured by gas chromatography: 63.4%) (yield based on theoretical amount: 94%).

後処理

  1. customA 500 mL four-necked flask equipped with a stirrer
  2. temperaturecooled
  3. customto remove amines
  4. customseparating the mixture into two layers
  5. washThe thus separated organic layer was washed with water
  6. customfurther separated into two layers

出典と根拠

ORDレコード
ord-cbf5812599834280bcff886e2231a5dd
出典データセット
uspto-grants-2010_06
特許番号
US07732644B2

関連ノート

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