Sodium Hydroxide → HCID 67214180, compound

HRID 2421517Notes

Reaction equation

HRID 2421517 reaction equation
[CH3:1][S:2][CH:3]([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([CH3:17])=[C:12]([CH3:18])[CH:11]=1)[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>C1COCC1.O>[CH3:1][S:2][CH:3]([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([CH3:17])=[C:12]([CH3:18])[CH:11]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67214404HCID 67214404, compound

Product 1

HCID 67214180HCID 67214180, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The product from Step 2 (2.0 g) in THF (10 ml) and water (3 ml) containing sodium hydroxide (0.4 g) were stirred at 60° C. for 2 hours then cooled to ambient temperature, evaporated under reduced pressure, diluted with water and washed with diethyl ether. The aqueous fraction was acidified with dilute hydrochloric acid and extracted with ethyl acetate (three times). The extracts were combined, washed with brine, dried over magnesium sulphate, then evaporated to give 2-methylthio-2-(3,4,5-trimethylphenoxy)acetic acid, 1.05 g, as a yellow gum. A portion of the gum was fractionated by chromatography (silica; ethyl acetate then methanol) to provided an analytical sample and the remainder used in the next stage without further purification.

Workup

  1. temperaturethen cooled to ambient temperature
  2. customevaporated under reduced pressure
  3. additiondiluted with water
  4. washwashed with diethyl ether
  5. extractionextracted with ethyl acetate (three times)
  6. washwashed with brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-9bd54a17dd3746cabf7d1ac7893d85f9
Source dataset
uspto-grants-2011_06
Patent number
US07956188B2

Reaction notes

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