Toluene → 4-Hexenoic acid, 2-isopropenyl-5-methyl-, ethyl ester

HRID 2273833ノート

反応式

HRID 2273833 の反応式
[C:1]([CH:4]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[C:5]([OH:7])=[O:6])([CH3:3])=[CH2:2].C(=O)([O-])[O-].[K+].[K+].[C:19]1(C)C=CC=C[CH:20]=1.S(OCC)(OCC)(=O)=O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([CH:4]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[C:5]([O:7][CH2:19][CH3:20])=[O:6])([CH3:3])=[CH2:2]

参加物

7

反応物 4

HCID 1140TolueneHCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 30138945-Methyl-2-(prop-1-en-2-yl)hex-4-enoic acid

生成物 1

HCID 30140494-Hexenoic acid, 2-isopropenyl-5-methyl-, ethyl ester収率 97%

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 962Water溶媒

実験手順

In a nitrogen atmosphere, a mixture of 200.01 g of 2-isopropenyl-5-methyl-4-hexenoic acid (1) having a purity of 85.4%, 89.82 g of potassium carbonate, 11.28 g of tetrabutylammonium chloride, and 800 g of toluene was heated to from 95° C. to 100° C., while being stirred, and then 191.8 g of diethyl sulfate was added dropwise thereto over 35 minutes. The reaction mixture was heated continuously for 2 hours, then cooled to room temperature, and subjected to addition of 510 g of water. The toluene solution was separated from the resulting mixture and then subjected to typical work-up including washing, drying and concentration to obtain the crude product. The crude product was distilled under reduced pressure to obtain 193.4 g of the intended product having a purity of 99.7%. The yield was 97%.

後処理

  1. temperaturewas heated to from 95° C. to 100° C.
  2. temperatureThe reaction mixture was heated continuously for 2 hours
  3. customThe toluene solution was separated from the resulting mixture
  4. washincluding washing
  5. customdrying
  6. concentrationconcentration
  7. customto obtain the crude product
  8. distillationThe crude product was distilled under reduced pressure

出典と根拠

ORDレコード
ord-c7ac0fb1b4434935b23c2c3d91fab189
出典データセット
uspto-grants-2015_09
特許番号
US09126923B2

反応ノート

読み込み中…