Ethanol → 4-(2-Fluorophenyl)butanoic acid

HRID 331240

Reaction equation

HRID 331240 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10](C(OC)=O)[C:11]([O:13]C)=[O:12].[OH-].[Na+].C(O)C>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 68704652Dimethyl 2-[2-(2-fluorophenyl)ethyl]malonate

Product 1

HCID 154910364-(2-Fluorophenyl)butanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl 2-[2-(2-fluorophenyl)ethyl]malonate, sodium hydroxide (22.7 g), ethanol (150 ml) and water (100 ml) were heated under reflux for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was acidified with hydrochloric acid, and extracted with chloroform. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 4-(2-fluorophenyl)butanoic acid.

Workup

  1. temperatureunder reflux for 1.5 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with chloroform
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c468c92760b24edfb6d15c08c6986f80
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Linked notes

Loading…