Sodium Hydroxide → 8-Methylsulfonyl-12-hydroxy-5-heptadecynoic acid

HRID 65644Notes

Reaction equation

HRID 65644 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][C:7]#[C:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])(=[O:4])=[O:3].[OH-].[Na+]>O.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][C:7]#[C:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21317523HCID 21317523, compound

Product 1

HCID 213176278-Methylsulfonyl-12-hydroxy-5-heptadecynoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 8-methylsulfonyl-12-acetoxy-5-heptadecynoate (41.6 g., 0.10 mole) is added to a solution of sodium hydroxide (12.0 g., 0.3 mole) in water (120 ml.) and methanol (600 ml.). The resulting solution is heated at 55°-60° C. for 24 hours. Most of the methanol is removed by evaporation in vacuo. The residue is diluted with water and extracted with ether. The aqueous solution is acidified with concentrated hydrochloric acid. The product which separates is taken up in ether, washed with water and dried over sodium sulfate. Evaporation of the ether in vacuo leaves the title compound as a viscous yellow oil. Purification is effected by column chromatography on silica gel with 2% methanol in chloroform as eluant. The title compound is obtained as a nearly colorless viscous oil.

Workup

  1. temperatureThe resulting solution is heated at 55°-60° C. for 24 hours
  2. customMost of the methanol is removed by evaporation in vacuo
  3. additionThe residue is diluted with water
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the ether in vacuo

Sources & evidence

ORD record
ord-b6d62277561a48ee8102289c9f51c685
Source dataset
uspto-grants-1978_12
Patent number
US04128564

Reaction notes

Loading…