Reaction #1929053

Reaction equation

16-hydroxyhexadecanoic acid

methanol

→

16-hydroxyhexadecanoic acid methyl ester

Yield 92.0%

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise at 0° C. within 2 min
2. 2
   OtherSubsequently the mixture was evaporated to dryness
3. 3
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (100 ml)
4. 4
   Washwashed with saturated sodium bicarbonate solution (2×50 ml) and Brine solution (1×50 ml)
5. 5
   DryingAfter drying over sodium sulfate the collected organic layer
6. 6
   Otherwas evaporated to dryness and vacuum
7. 7
   Otherdried at room temperature

Procedure

To a cooled (0° C.) solution of 16-hydroxyhexadecanoic acid (3000 mg, 10.79 mmol) in anhydrous methanol (27 ml) acetyl chloride (3.837 ml, 53.96 mmol) was added dropwise at 0° C. within 2 min, then the mixture was stirred at room temperature for 3.5 hrs under Ar-atmosphere. Subsequently the mixture was evaporated to dryness, the residue was dissolved in dichloromethane (100 ml), washed with saturated sodium bicarbonate solution (2×50 ml) and Brine solution (1×50 ml). After drying over sodium sulfate the collected organic layer was evaporated to dryness and vacuum dried at room temperature. Yield: 92% (white solid).

Source