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

HRID 2083319Notes

Reaction equation

HRID 2083319 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-80cf603d62254d699be08e20e67e8899
Source dataset
uspto-grants-1978_04
Patent number
US04085125

Reaction notes

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