Reaction #155411

Reaction equation

4-bromomethylbenzaldehyde

4-hydroxythiophenol

triethylamine

→

title compound

Yield 62.0%

4-{[(4-Hydroxyphenyl)thio]methyl}benzaldehyde

Yield 62.0%

Solvents

1,4-dioxane

water

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate (2-fold 20 mL)
2. 2
   WashThe combined organic extracts were washed with brine
3. 3
   Dryingdried (sodium sulphate)
4. 4
   Otherthe solvent removed in vacuo
5. 5
   OtherThe crude material was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (9:1 changing to 0:1, by volume)

Procedure

A solution of 4-bromomethylbenzaldehyde (0.3 g, 1.5 mmol) and 4-hydroxythiophenol (0.2 g, 1.5 mmol) in 1,4-dioxane (10 mL) was degassed and treated with triethylamine (0.44 mL, 3.11 mmol). After stirring for 1 day the mixture was diluted with water (20 mL) and extracted with ethyl acetate (2-fold 20 mL). The combined organic extracts were washed with brine and dried (sodium sulphate) and the solvent removed in vacuo. The crude material was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (9:1 changing to 0:1, by volume) to give the title compound as a solid, 62% yield, 220 mg.

Source