Methanol → Methyl 16-hydroxyhexadecanoate

HRID 1841871Notes

Reaction equation

HRID 1841871 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].[CH3:20]O>>[CH3:20][O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1]

Participants

3

Reactant 2

HCID 887MethanolHCID 1046616-Hydroxyhexadecanoic acid

Product 1

HCID 3496888Methyl 16-hydroxyhexadecanoateYield 92%

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).

Workup

  1. additionwas added dropwise at 0° C. within 2 min
  2. customSubsequently the mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in dichloromethane (100 ml)
  4. washwashed with saturated sodium bicarbonate solution (2×50 ml) and Brine solution (1×50 ml)
  5. dry with materialAfter drying over sodium sulfate the collected organic layer
  6. customwas evaporated to dryness and vacuum
  7. customdried at room temperature

Sources & evidence

ORD record
ord-4ec2919b59924103a324e7f0b7ff07ad
Source dataset
uspto-grants-2015_02
Patent number
US08945897B2

Reaction notes

Loading…