Hydrochloric Acid → 2-(4-Fluorophenyl)malonic acid

HRID 627539Notes

Reaction equation

HRID 627539 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]([O:16]CC)=[O:15])[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]([OH:11])=[O:10])[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2782660Diethyl 2-(4-fluorophenyl)malonate

Product 1

HCID 153925382-(4-Fluorophenyl)malonic acid

Conditions

Temperature
50 °C

Procedure

A mixture of diethyl 2-(4-fluorophenyl)malonate (2.98 g, 8.204 mmol, Intermediate 59, step a) and an aqueous 3 M NaOH solution (5 mL) were stirred in a 50° C. oil bath for 48 hours, cooled to RT, poured into ice water and acidified with 6N HCl. The aqueous mixture was extracted with EtOAc. The EtOAc extract was dried over Na2SO4, filtered, and evaporated in vacuo to provide the title compound.

Workup

  1. temperaturecooled to RT
  2. extractionThe aqueous mixture was extracted with EtOAc
  3. extractionThe EtOAc extract
  4. dry with materialwas dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-66d540573e9345a7b1f126ba1fd1ed47
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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