反应 #83280

反应方程式

phthalic anhydride

aluminum chloride

ether

1,3-diethylbenzene

→

2-(2,4-diethylbenzoyl)benzoic acid

收率 93.0%

溶剂

tetrachloroethane

tetrachloroethane

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred for 2 hours
2. 2
   workup.ADDITIONwas added
3. 3
   过滤the mixture was filtered
4. 4
   其他The organic layer was separated
5. 5
   洗涤washed with saturated Na2CO3 (6×)
6. 6
   萃取the basic layer was extracted with CH2Cl2
7. 7
   萃取the CH2Cl2 layer was extracted with 2N NaOH
8. 8
   萃取the mixture was extracted with ether
9. 9
   浓缩concentrated in vacuo
10. 10
    过滤filtered
11. 11
    洗涤rinsed with hexane

实验过程

To a cooled mixture of phthalic anhydride (50 g, 0.34 mol) and aluminum chloride (99 g) in tetrachloroethane (300 mL) was added dropwise 1,3-diethylbenzene (50 g) over 11/4 hours. The mixture was stirred in an ice bath for 30 minutes, additional tetrachloroethane was added, and the mixture was stirred for 2 hours. The reaction mixture was poured into concentrated HCl/ice (1 L), ether (500 mL) was added and the mixture was filtered. The organic layer was separated, washed with saturated Na2CO3 (6×), the basic layer was extracted with CH2Cl2 and the CH2Cl2 layer was extracted with 2N NaOH and the 2N NaOH layer was acidified. The basic layer was acidified with aqueous HCl, this acidic layer was combined with the above acidified 2N NaOH layer and the mixture was extracted with ether. The CH2Cl2 layer and the ether layer were combined and concentrated in vacuo. The residue was slurried with water, filtered and rinsed with hexane to afford 88.8 g (93%) of 2-(2,4-diethylbenzoyl)benzoic acid, m.p. 115°-118° C.

来源