Reaction #1729

Reaction equation

3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid

benzyl 6-hydroxy-nicotinate

dicyclohexylcarbodiimide

→

benzyl 6-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinate

Yield 57.0%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   workup.ADDITIONpoured into ice-cold aqueous ammonium chloride solution
2. 2
   Extractionextracted several times with ether
3. 3
   Washwashed with water
4. 4
   Dryingdried over sodium sulfate
5. 5
   Otherevaporated
6. 6
   FiltrationThe crude product, for the most part crystalline, was filtered over silica gel (eluent hexane/ethyl acetate=9:1)
7. 7
   Otherrecrystallized from hexane
8. 8
   Othercrystallization of the mother liquor

Procedure

6 g of 3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid were dissolved in 180 ml of methylene chloride. After the addition of a solution of 4.8 g of benzyl 6-hydroxy-nicotinate in 160 ml of methylene chloride and of 2.3 g of 4-dimethylaminopyridine, the solution was cooled to 0° C. and treated with 4.4 g of dicyclohexylcarbodiimide. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours, thereafter poured into ice-cold aqueous ammonium chloride solution, extracted several times with ether, washed with water, dried over sodium sulfate and evaporated. The crude product, for the most part crystalline, was filtered over silica gel (eluent hexane/ethyl acetate=9:1) and recrystallized from hexane. After repeated crystallization of the mother liquor there were obtained all together 5.7 g of benzyl 6-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinate in colorless crystals, m.p. 94°-95° C.

Source