Reacción #939022

Ecuación de reacción

1,2-cyclohexanedicarboxylic acid monohexadecyl ester

tetrahydrofuran

→

cyclohexane-1,2-dicarboxylic acid monoethyl ester monohexadecyl ester

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas treated with oxalyl choloride (5 g) overnight at room temperature
2. 2
   OtroAfter solvent removal in vacuuo the resultant acid chloride
3. 3
   workup.DISSOLUTIONwas dissolved in 50 ml of absolute ethanol
4. 4
   workup.ADDITIONsodium carbonate (2.2 g) was added
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuuo
7. 7
   workup.DISSOLUTIONThe light yellow liquid product was dissolved in hexane
8. 8
   OtroSolvent removal

Procedimiento

A mixture of 1,2-cyclohexanedicarboxylic acid monohexadecyl ester (white solid m.p.=54-55° C.) (8 g) (prepared from 1,2-cyclohexanedicarboxylic anhydride (1 eq), hexadecanol (1 eq), triethylamine (1 eq), in ethyl acetate at room temperature for 24 hours) in 50 ml of tetrahydrofuran was treated with oxalyl choloride (5 g) overnight at room temperature. After solvent removal in vacuuo the resultant acid chloride was dissolved in 50 ml of absolute ethanol, and sodium carbonate (2.2 g) was added. The mixture was stirred for 3 hours, filtered and concentrated in vacuuo. The light yellow liquid product was dissolved in hexane and passed through a pad of silica gel. Solvent removal gave cyclohexane-1,2-dicarboxylic acid monoethyl ester monohexadecyl ester (5.3 g) as a clear colorless liquid which forms a waxy solid when cooled to below room temperature.

Fuente