Ethylparaben → Benzoic acid, 4-[(3-methyl-2-butenyl)oxy]-, ethyl ester

HRID 41375

反応式

HRID 41375 の反応式
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]([CH3:24])=[CH:21][CH2:22]Cl>C(#N)C>[CH3:19][C:20]([CH3:24])=[CH:21][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 8434EthylparabenHCID 104291-Chloro-3-methyl-2-buteneHCID 11430Potassium Carbonate

生成物 1

HCID 13203109Benzoic acid, 4-[(3-methyl-2-butenyl)oxy]-, ethyl ester収率 95.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Ethyl 4-hydroxybenzoate (1.66 g, 10.0 mmol) and anhydrous potassium carbonate (2.07 g, 15.0 mmol) in acetonitrile (30 ml) was treated with 3-methyl-2-butenyl chloride (1.35 ml, 12.0 mmol) and the mixture was stirred and held at reflux for 3 hours. Upon cooling the solvent was removed in vacuo and the mixture partitioned between dichloromethane and water. The organics were separated and the solvent removed in vacuo to afford ethyl 4-(3-methyl-but-2-enyloxy)-benzoate (2.23 g, 95%) as a pale yellow liquid which was used without further purification. 1H NMR (DMSO-d6) 7.89 (2H, d), 7.04 (2H, d), 5.44 (1H, t), 4.62 (2H, d), 4.28 (2H, q), 1.77 (3H, s), 1.73 (3H, s), 1.31 (3H, t). MS: [M+H]+ 235.

後処理

  1. temperatureat reflux for 3 hours
  2. temperatureUpon cooling the solvent
  3. customwas removed in vacuo
  4. customthe mixture partitioned between dichloromethane and water
  5. customThe organics were separated
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-a8c909eaca664dc2a9a6be3fc4c15e79
出典データセット
uspto-grants-2013_09
特許番号
US08530469B2

関連ノート

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