16-Hydroxyhexadecanoic acid → 16-Methanesulfonyloxyhexadecanoic acid

HRID 1780697Notes

Reaction equation

HRID 1780697 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][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:20][S:21]([O: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])(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 1046616-Hydroxyhexadecanoic acidHCID 31297Methanesulfonyl chloride

Product 1

HCID 1904721116-Methanesulfonyloxyhexadecanoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

16-Hydroxyhexadecanoic acid (1 g) dissolved in a 10% hydrochloric acid-methanol solution was stirred at room temperature for 1 hour. The mixture was then concentrated and distributed into chloroform and water, and the chloroform layer was washed with a 1% aqueous sodium hydrogen carbonate solution and water, dried with anhydrous sodium sulfate and concentrated to give the methyl ester of 16-hydroxyhexadecanoic acid (1.02 g). To the methyl ester of 16-hydroxyhexadecanoic acid dissolved in pyridine (20 ml) was added methanesulfonyl chloride (0.50 g), and the mixture was stirred for 8 hours. Then, the pyridine was removed by distillation, and the residue was distributed into chloroform and water. The chloroform layer was dried with anhydrous sodium sulfate, concentrated and subjected to chromatography on a silica gel column with an eluent system of n-hexane-ethyl acetate (50:1) to give the methyl ester of 16-methanesulfonyloxy hexadecanoic acid (1.02 g).

Workup

  1. customThen, the pyridine was removed by distillation
  2. dry with materialThe chloroform layer was dried with anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0254d0ce63fa471dba56770add46dffe
Source dataset
uspto-grants-1997_05
Patent number
US05631238

Reaction notes

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