Potassium Hydroxide → 3-[(4-Fluorophenyl)thio]-2-hydroxy-2-methylpropanoic acid

HRID 23225

Reaction equation

HRID 23225 reaction equation
FC1C=CC(S)=CC=1.[H-].[Na+].[OH:11][C:12]([CH3:26])([CH2:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:13]([O:15]C)=[O:14].[OH-].[K+]>C(O)C>[OH:11][C:12]([CH3:26])([CH2:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 677894-FluorothiophenolHCID 21966928Methyl 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionate

Product 1

HCID 98133673-[(4-Fluorophenyl)thio]-2-hydroxy-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The methyl 2-methyl-oxirane-carboxylate of formula (1), which was obtained by epoxidation, was reacted with 4-fluorothiophenol [formula (2)] in the presence of sodium hydride under the conditions listed in Scheme-2. The obtained methyl 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionate of formula (3) was hydrolyzed with potassium hydroxide in aqueous ethanol over a period of 22 hours to yield the 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionic acid of formula (4), which was converted into the acid chloride of formula (5) with thionyl chloride in dimethyl acetamide at −15° C.

Sources & evidence

ORD record
ord-d9bf239859a04e2a81149bb8993c3a57
Source dataset
uspto-grants-2005_02
Patent number
US06849763B2

Linked notes

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