Hydrochloric Acid → 3-(2,4-difluorophenyl)propanoic Acid

HRID 974393Notes

Reaction equation

HRID 974393 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([O:13]CC)=[O:12].[OH-].[Na+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723671Tetrabutylammonium HydroxideHCID 19986449Ethyl 3-(2,4-difluorophenyl)propanoate

Product 1

HCID 49863953-(2,4-difluorophenyl)propanoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

33 g (0.154 mol) of ethyl 3-(2,4-difluorophenyl)propanoate are suspended in 250 ml of water. 60 ml of 10N sodium hydroxide solution and 30 ml of 40% tetrabutylammonium hydroxide solution are then added. The mixture is stirred vigorously and warmed. Everything has dissolved at about 50° C. The mixture is warmed further to 80° C. and then cooled to 5° C. On dropwise addition of 80 ml of concentrated hydrochloric acid, white crystals precipitate, which are filtered off and washed with ice-water. After drying in vacuo, 28.1 g (98% of theory) of white crystals of melting point 107°-108° C., which does not change even after recrystallization from 50% ethanol, are obtained.

Workup

  1. temperaturewarmed
  2. dissolutionEverything has dissolved at about 50° C
  3. temperaturecooled to 5° C
  4. filtrationare filtered off
  5. washwashed with ice-water
  6. customAfter drying in vacuo, 28.1 g (98% of theory) of white crystals of melting point 107°-108° C., which
  7. customafter recrystallization from 50% ethanol
  8. customare obtained

Sources & evidence

ORD record
ord-507b747fd2eb4eb2888acbbc79b1f690
Source dataset
uspto-grants-1991_11
Patent number
US05068371

Reaction notes

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