Sodium Hydroxide → 12-Hydroxy-8-(methanesulfonyl)heptadecanoic acid

HRID 65638Notes

Reaction equation

HRID 65638 reaction equation
[CH3:1][S:2]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([O:25]C(=O)C)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])(=[O:4])=[O:3].[OH-].[Na+]>CO>[CH3:1][S:2]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21317665HCID 21317665, compound

Product 1

HCID 2021027912-Hydroxy-8-(methanesulfonyl)heptadecanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 8-methylsulfonyl-12-acetoxyheptadecanoate (29.4 g., 0.07 mole) and 20% aqueous sodium hydroxide (70 ml.) in methanol (70 ml.) is stirred at room temperature for 17 hours. The resulting solution is evaporated in vacuo at ~100° C. to an oily residue which is dissolved in water. The aqueous solution is extracted with ether and the organic extract discarded. Then, the aqueous phase is acidified to Congo Red with 6N hydrochloric acid and extracted with ether. The organic extract is washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo at ~100° C. providing crude title compound as a viscous oil (23.6 g., 93%).

Workup

  1. customThe resulting solution is evaporated in vacuo at ~100° C. to an oily residue which
  2. dissolutionis dissolved in water
  3. extractionThe aqueous solution is extracted with ether
  4. extractionthe organic extract
  5. extractionextracted with ether
  6. extractionThe organic extract
  7. washis washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo at ~100° C.

Sources & evidence

ORD record
ord-dda08eabadb84d75822c615cbb4e3989
Source dataset
uspto-grants-1978_12
Patent number
US04128564

Reaction notes

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