Sulfuric Acid → 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

HRID 440156

反応式

HRID 440156 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](N)=[CH:5][CH:4]=1.S(=O)(=O)(O)O.C(C(CCCC)CO)C.N(OCCCCC)=O.[C:32]([O:36][CH2:37][CH:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][CH3:42])(=[O:35])[CH:33]=[CH2:34]>O.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:34]=[CH:33][C:32]([O:36][CH2:37][CH:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][CH3:42])=[O:35])=[CH:5][CH:4]=1

参加物

8

反応物 5

HCID 1118Sulfuric AcidHCID 76362-Ethylhexyl acrylateHCID 77202-EthylhexanolHCID 7732P-AnisidineHCID 10026Pentyl nitrite

生成物 1

HCID 216302-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

反応条件

温度
10 °C

実験手順

12.3 g of 4-anisidine (4-methoxyaniline) are mixed with stirring with 10 ml of concentrated sulfuric acid and 60 ml of 2-ethylhexanol and the mixture is cooled to about 10° C. 11.7 g of amyl nitrite are then slowly added and the mixture is stirred for a further 40 minutes after addition is completed. 20.2 g of 2-ethylhexyl acrylate and 100 mg of Pd (5% by weight of Pd on activated charcoal) are then added to the reaction mixture which is heated in the course of 1 hour to 65° C. and stirred for 12 hours at this temperature. The mixture is diluted with 100 ml of water and extracted with 200 ml of dichloromethane. As studies by thin-layer chromatography and gas chromatography show, 2-ethylhexyl p-methoxycinnamate has not formed even in the smallest amounts. The 2-ethylhexyl acrylate used is present essentially in unchanged form.

後処理

  1. additionafter addition
  2. temperatureis heated in the course of 1 hour to 65° C.
  3. stirringstirred for 12 hours at this temperature
  4. extractionextracted with 200 ml of dichloromethane

出典と根拠

ORDレコード
ord-7bfe1daee73a4841b532e7b6e837d8c6
出典データセット
uspto-grants-1996_05
特許番号
US05516932

関連ノート

読み込み中…