Sodium Hydroxide → HCID 10877456, compound

HRID 2395241Notes

Reaction equation

HRID 2395241 reaction equation
C([S:4][CH2:5][CH:6]([CH2:10][C:11]([OH:13])=[O:12])[C:7]([OH:9])=[O:8])(=O)C.[OH-].[Na+]>O>[SH:4][CH2:5][CH:6]([CH2:10][C:11]([OH:13])=[O:12])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15307653192879-20-2

Product 1

HCID 10877456HCID 10877456, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

582 g (2.85 mol) of acetylthiomethylbutanedioic acid (VII) are added, under nitrogen and while cooling with ice, to a solution of 570 g (14.25 mol) of NaOH in 3 litres of water (exothermic reaction). After 15 hours' stirring at room temperature, the reaction mixture is acidified to pH 1 with concentrated hydrochloric acid and extraction is carried out with ether. The combined organic phases are dried over sodium sulfate and concentrated to dryness, and the crystalline residue is washed with 200 ml of cold dichloromethane. There are obtained 385 g of crystals having a melting point of 107°-108.5° C.

Workup

  1. extractionthe reaction mixture is acidified to pH 1 with concentrated hydrochloric acid and extraction
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. washthe crystalline residue is washed with 200 ml of cold dichloromethane

Sources & evidence

ORD record
ord-167c631227634bc0a1fe18afc2fa3d06
Source dataset
uspto-grants-1998_09
Patent number
US05814629

Reaction notes

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