Reaction #3157

Reaction equation

triethylamine

(2-hydroxybenzyl)triphenylphosphonium bromide

nonanoic anhydride

→

2-octylbenzofuran

Yield 76.6%

Solvents

toluene

Conditions

Workup

1. 1
   Temperatureby refluxing for 4.5 hours
2. 2
   OtherAfter the reaction
3. 3
   workup.WAITthe reaction mixture was left
4. 4
   Otherstanding at room temperature
5. 5
   Otherto precipitate a crystal
6. 6
   OtherThe crystal was removed by filtration
7. 7
   ConcentrationThe filtrate was concentrated
8. 8
   Otherpurified by silica gel column chromatography (eluent:toluene/hexane=1/1)

Procedure

112 g (249 mM) of (2-hydroxybenzyl)triphenylphosphonium bromide, 83 g (278 mM) of nonanoic anhydride, 104 g (1.03 mM) of triethylamine and 800 ml of toluene were placed in a 3 1-three-necked flask, followed by refluxing for 4.5 hours under stirring. After the reaction, the reaction mixture was left standing at room temperature to precipitate a crystal. The crystal was removed by filtration. The filtrate was concentrated and purified by silica gel column chromatography (eluent:toluene/hexane=1/1) to obtain 44 g of liquid 2-octylbenzofuran (Yield: 76.6%).

Source