Hydrochloric Acid → 3-(2',4'-Difluoro-4-biphenylyl)butyric acid

HRID 26906Notes

Reaction equation

HRID 26906 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])=[CH:11][CH:10]=1)(O)[CH3:7])C.Cl.O=S(Cl)Cl>ClCCl>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([CH:6]([CH3:7])[CH2:5][C:4]([OH:23])=[O:3])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 538342513-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester

Product 1

HCID 213225403-(2',4'-Difluoro-4-biphenylyl)butyric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.2 g. of 3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester in 10 ml. of dichloromethane is saturated with dry HCl gas and 1 ml. of SOCl2 is added. The mixture is warmed to 50° for 2 hours and solvent is removed. The residue, 3'(2',4'-difluoro-4-biphenylyl)-3-chlorobutyric acid ethyl ester, is dissolved in 100 ml. of methanol and hydrogenated on 100 mg. of platinum oxide under normal pressure at 25°. The precipitate is filtered off. A solution of 0.4 g. of NaOH in 5 ml. of water is added to the filtrate. The mixture is heated under reflux for 2 hours and evaporated and the residue is dissolved in water and worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)butyric acid, m.p. 109°-110°.

Workup

  1. temperatureThe mixture is warmed to 50° for 2 hours
  2. customsolvent is removed
  3. dissolutionThe residue, 3'(2',4'-difluoro-4-biphenylyl)-3-chlorobutyric acid ethyl ester, is dissolved in 100 ml
  4. customat 25°
  5. filtrationThe precipitate is filtered off
  6. additionof water is added to the filtrate
  7. temperatureThe mixture is heated
  8. temperatureunder reflux for 2 hours
  9. customevaporated
  10. dissolutionthe residue is dissolved in water

Sources & evidence

ORD record
ord-e0294fb09a194e28930f7334cb83d6fc
Source dataset
uspto-grants-1979_04
Patent number
US04151302

Reaction notes

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