反応 #83280

反応方程式

phthalic anhydride

aluminum chloride

ether

1,3-diethylbenzene

→

2-(2,4-diethylbenzoyl)benzoic acid

収率 93.0%

溶媒

tetrachloroethane

tetrachloroethane

反応条件

後処理

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

実験手順

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.

出典