Reaction #422019

Reaction equation

2-(5-Chloro-2H-benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol

2-ethylhexanol

Sodium carbonate

→

2-(5-Chloro-benzotriazol-2-yl)-6-(2-ethylhexyloxymethyl)-4-methyl-phenol

Yield 76.2%

Solvents

acetone

Conditions

Workup

1. 1
   workup.STIRRINGThe slightly yellow reaction mixture is stirred at 80° C. for 3 hours
2. 2
   Otherevaporated to dryness
3. 3
   workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
4. 4
   Extractionextracted with aqueous citric acid (5%) and brine
5. 5
   DryingThe organic layer is dried over sodium sulphate
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated to dryness
8. 8
   OtherThe crude product is purified by column chromatography (ethyl acetate/heptane 1:12)

Procedure

2-(5-Chloro-2H-benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol (5.0 g, 16 mmol) is suspended in a mixture of 2-ethylhexanol (20.0 g, 154 mmol) and acetone (5 g) and stirred at 80° C. for 15 minutes. Sodium carbonate (3.4 g, 32 mmol) is added. The slightly yellow reaction mixture is stirred at 80° C. for 3 hours and evaporated to dryness. The residue is dissolved in ethyl acetate and extracted with aqueous citric acid (5%) and brine. The organic layer is dried over sodium sulphate, filtered and evaporated to dryness. The crude product is purified by column chromatography (ethyl acetate/heptane 1:12) to yield 4.9 g of 2-(5-Chloro-benzotriazol-2-yl)-6-(2-ethylhexyloxymethyl)-4-methyl-phenol.

Source