Sodium Hydroxide → 8-Methylsulfonyl-12-hydroxy-13-(3-trifluoromethylphenoxy)tridecanoic acid

HRID 328802Notes

Reaction equation

HRID 328802 reaction equation
[CH3:1][S:2]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([O:32]C(=O)C)[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1)[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:32])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=1)[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 21317521Methyl 8-methylsulfonyl-12-acetoxy-13-(3-trifluoromethylphenoxy)tridecanoate

Product 1

HCID 213175568-Methylsulfonyl-12-hydroxy-13-(3-trifluoromethylphenoxy)tridecanoic acidYield 62.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 8-methylsulfonyl-12-acetoxy-13-(3-trifluoromethylphenoxy)tridecanoate (9.90 g., 0.019 mole), 20% aqueous sodium hydroxide (30 ml.) and methanol (30 ml.) is stirred at room temperature overnight. Then the reaction mixture is concentrated in vacuo on a steam bath. The concentrate is dissolved in water and extracted with ether. The basic aqueous solution is acidified with 6N hydrochloric acid and extracted with ether. These ether extracts are washed with water until neutral, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (5.55 g., 0.0118 mole, 62%) in analytical purity.

Workup

  1. concentrationThen the reaction mixture is concentrated in vacuo on a steam bath
  2. dissolutionThe concentrate is dissolved in water
  3. extractionextracted with ether
  4. extractionextracted with ether
  5. washThese ether extracts are washed with water until neutral,
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a730ebef8b14cfdb76f6427dd80bc77
Source dataset
uspto-grants-1977_04
Patent number
US04018802

Reaction notes

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