Reaction #42772

Reaction equation

sodium acetate

resorcinol

4-chlorophenylacetic acid

boron trifluoride etherate

→

title compound

2-(4-Chlorophenyl)-1-(2,4-dihydroxyphenyl)-ethanone

Conditions

Workup

1. 1
   Temperatureto cool to room temperature
2. 2
   workup.STIRRINGThe suspension is stirred overnight at room temperature
3. 3
   OtherThe orange brown precipitate is removed by filtration
4. 4
   Otherdried in vacuo
5. 5
   Othertriturated with isopropyl ether/hexane (1:9)
6. 6
   Otherto give a yellow solid
7. 7
   WashThis solid is washed with hexane
8. 8
   Otherdried in vacuo

Procedure

A mixture of resorcinol (100 g, 0.908 mol), 4-chlorophenylacetic acid (170 g, 0.999 mol) and boron trifluoride etherate is stirred mechanically at 85° C. for 1.75 h. The dark red-brown reaction mixture is allowed to cool to room temperature and then poured slowly into aqueous sodium acetate (1 l, 30% w/v). The suspension is stirred overnight at room temperature. The orange brown precipitate is removed by filtration, dried in vacuo and then triturated with isopropyl ether/hexane (1:9) to give a yellow solid. This solid is washed with hexane and dried in vacuo to provide the title compound. A further three crops of material are obtained from the sodium acetate work-up mixture.

Source