海萝胶 → 2-Ethyl-4-phenyl-1-indanone

HRID 964776

反应方程式

HRID 964776 反应方程式
[C:1]1([C:7]2[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=2CC(CC)C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=[O:21].[Al+3].[Cl-].[Cl-].[Cl-].Cl.[C:29]1([CH3:35])[CH:34]=CC=[CH:31][CH:30]=1>>[CH2:30]([CH:29]1[CH2:35][C:8]2[C:16](=[CH:17][CH:18]=[CH:19][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:34]1=[O:21])[CH3:31]

参与物

6

反应物 5

HCID 313海萝胶HCID 1140甲苯HCID 24386氯化亚砜HCID 6451240三氯化铝HCID 215719833-(2-Biphenylyl)-2-ethylpropionic acid

产物 1

HCID 221732182-Ethyl-4-phenyl-1-indanone收率 85%

反应条件

温度
80 °C

实验过程

A solution of 236 g (0.93 mol) of 13 in 81 cm3 (1.2 mol) of thionyl chloride was stirred at room temperature for 18 hours. Excess thionyl chloride was removed at 10 mbar and the oily residue was freed from adhering residues of thionyl chloride by repeated dissolution in 200 cm3 of toluene in each case and stripping off in vacuo. The acid chloride was taken up in 400 cm3 of toluene and added dropwise at 10° C. to a suspension of 133 g (1.0 mol) of AlCl3 in 2000 cm3 of toluene. The reaction mixture was heated at 80° C. for 1 hour, poured into 2000 g of ice and acidified to pH 1 by means of concentrated aqueous HCl. The organic phase was separated off, and the aqueous phase was then extracted three times with 200 cm3 of Et2O in each case. The combined organic phases were washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution and subsequently dried (MgSO4), giving 187 g (85%) of 14, which was reacted further without further purification.

后处理

  1. customExcess thionyl chloride was removed at 10 mbar
  2. dissolutionby repeated dissolution in 200 cm3 of toluene in each case
  3. customThe organic phase was separated off
  4. extractionthe aqueous phase was then extracted three times with 200 cm3 of Et2O in each case
  5. washThe combined organic phases were washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  6. dry with materialsubsequently dried (MgSO4)

来源与证据

ORD记录
ord-cbfd08e87ed24727b7e94e64147d009a
来源数据集
uspto-grants-1998_06
专利号
US05770753

关联笔记

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