Reaction #2314291

Reaction equation

phenol

(4-(trans-4-Pentylcyclohexyl)butyl]phenol

(4-(4-Methyl-3-pentenyl)-1-cyclohexenyl)carboxylic acid

dicyclohexylcarbodiimide

dimethylaminopyridine

→

4-(4-pentylcyclohexyl)butylphenyl (4-pentyl-1-cyclohexenyl)carboxylate

Solvents

tetrahydrofuran

water

Conditions

Workup

1. 1
   OtherTo a round-bottom flask equipped with a stirbar
2. 2
   Extractionextracted with 1:1 hexanes
3. 3
   WashThe combined organic layers are washed with brine
4. 4
   Dryingdried over potassium carbonate
5. 5
   Concentrationthe solution is concentrated in vacuo
6. 6
   FiltrationFiltration through silica gel using 10% ethyl acetate in hexanes
7. 7
   Othergives the pure product

Procedure

To a round-bottom flask equipped with a stirbar is added phenol 3H (R=pentyl) (5 g), (4-(4-Methyl-3-pentenyl)-1-cyclohexenyl)carboxylic acid (R=n-pentyl) (3.3 g), dicyclohexylcarbodiimide (5.11 g), dimethylaminopyridine (202 mg), and anhydrous tetrahydrofuran (50 mL). The reaction is stirred overnight, at which time the solution is poured into water and extracted with 1:1 hexanes:ethyl acetate. The combined organic layers are washed with brine and dried over potassium carbonate, and the solution is concentrated in vacuo. Filtration through silica gel using 10% ethyl acetate in hexanes gives the pure product.

Source