3-氯苯酚 → (E)-3-(3-chloro-phenoxy)-but-2-enoic acid ethyl ester

HRID 19264

反应方程式

HRID 19264 反应方程式
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.[CH2:15]([O:17][C:18](=[O:23])[CH:19]=[C:20](Cl)[CH3:21])[CH3:16]>O1CCCC1>[CH2:15]([O:17][C:18](=[O:23])/[CH:19]=[C:20](/[O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=1)\[CH3:21])[CH3:16]

参与物

5

反应物 3

HCID 79333-氯苯酚HCID 2828353-Chloro-but-2-enoic acid ethyl esterHCID 23665647叔丁醇钾

产物 1

HCID 66894928(E)-3-(3-chloro-phenoxy)-but-2-enoic acid ethyl ester收率 40.3%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

反应条件

温度
23 °C

实验过程

Potassium t-butoxide (7.40 g, 0.066 mol) was added to a stirred solution of 3-chloro-phenol (4.22 g, 0.033 mol) in tetrahydrofuran (35 mL) at 23° C. under nitrogen and the reaction mixture was heated to reflux for 0.75 h. The reaction mixture was cooled to 23° C. and a solution of 3-chloro-but-2-enoic acid ethyl ester (prepared as in Example 191, 5.00 g, 0.034 mol) in tetrahydrofuran (40 mL) was added to the reaction mixture. The reaction mixture was refluxed for an additional 3 h. After this time, the mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was then washed with 5% aqueous sodium hydroxide solution followed by a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to afford (E)-3-(3-chloro-phenoxy)-but-2-enoic acid ethyl ester (3.20 g, 40%) as a yellow oil.

后处理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 0.75 h
  3. temperatureThe reaction mixture was refluxed for an additional 3 h
  4. concentrationAfter this time, the mixture was concentrated in vacuo
  5. additionthe residue was diluted with water
  6. extractionextracted with diethyl ether
  7. washThe organic layer was then washed with 5% aqueous sodium hydroxide solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-480ba3fb100a46ff8c4148f1b557303a
来源数据集
uspto-grants-2010_06
专利号
US07741327B2

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