Acetic Acid → Methyl 8-methylsulfonyl-12-hydroxyheptadecanoate

HRID 263017Notes

Reaction equation

HRID 263017 reaction equation
[N+](=C)=[N-].[CH3:4][S:5]([CH:8]([CH2:18][CH2:19][CH2:20][CH:21]([OH:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])(=[O:7])=[O:6].[C:28](O)(=O)C>CCOCC>[CH3:4][S:5]([CH:8]([CH2:18][CH2:19][CH2:20][CH:21]([OH:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:28])=[O:16])(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 2021027912-Hydroxy-8-(methanesulfonyl)heptadecanoic acid

Product 1

HCID 21317548Methyl 8-methylsulfonyl-12-hydroxyheptadecanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (approximately 2.5 g., 0.06 mole) in ether (100 ml.) is mixed with a solution of 8-methylsulfonyl-12-hydroxyheptadecanoic acid (10.8 g., 0.03 mole) in ether (50 ml.). The resulting solution is allowed to stand 4 hours at room temperature. Acetic acid is then added to destroy the excess diazomethane and the solution is washed with dilute sodium bicarbonate solution and water and dried over sodium sulfate. Evaporation of volatile materials at reduced pressure yields methyl 8-methylsulfonyl-12-hydroxyheptadecanoate, a colorless viscous oil.

Workup

  1. customto destroy the excess diazomethane
  2. washthe solution is washed with dilute sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of volatile materials at reduced pressure

Sources & evidence

ORD record
ord-e36e520aaf3e4dcdbe2ebf147701cfa6
Source dataset
uspto-grants-1979_05
Patent number
US04155908

Reaction notes

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