Sulfuric Acid → HCID 24983445, compound

HRID 1925203Notes

Reaction equation

HRID 1925203 reaction equation
S(=O)(=O)(O)O.[C:6]1([CH3:16])C=CC(S(O)(=O)=O)=CC=1.[F:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]([CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:23])=[CH:20][CH:19]=1.C([O-])(O)=[O:33].[Na+].[OH-].[K+]>ClCCl.CO.C(O)CO.O>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]2([CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[O:33][CH2:6][CH2:16][O:23]2)=[CH:30][CH:31]=1

Participants

10

Reactant 5

HCID 1118Sulfuric Acid2×HCID 6101p-Toluenesulfonic acidHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 6890964-(4-Fluorobenzoyl)butyric Acid

Product 1

HCID 24983445HCID 24983445, compound

Reagents, catalysts & solvents 4

HCID 174Ethylene GlycolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In an inert water-free solvent, e.g. in dichloromethane in the presence of a strong acid, e.g. conc. sulphuric acid or p-toluene sulphonic acid, preferably conc. sulphuric acid and water-binding auxiliary material, e.g. trimethyl-ortho-formiate 4-(4-fluor-benzoil)-butyric acid (II) is reacted in one step with ethylene glycol at a 20-25° C. temperature. The reaction is stopped with addition of a base, e.g. NaHCO3. The solvent is changed to an alcoholic one, preferably to methanol, and the formed ester intermediate (III) is hydrolyzed by a base solution, preferably with potassium hydroxide solution. The formed 4-[2-(4-fluoro-phenyl)-[1,3]dioxolane-2-yl]-butyric acid (IV) is isolated after the concentration of the reaction mixture, then acidification with a weak acid, e.g. with tartaric acid, citric acid, preferably citric acid followed an extraction with an appropriate solvent, e.g. ethyl acetate. The product is purified by crystallization from an apolar solvent, e.g. from n-hexane or n-heptane.

Sources & evidence

ORD record
ord-693cbbe1f5c84cef8fda88621ab49127
Source dataset
uspto-grants-2012_05
Patent number
US08178665B2

Reaction notes

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