Hydrochloric Acid → 3-(2-Fluorophenyl)propanoic acid

HRID 1757455Notes

Reaction equation

HRID 1757455 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][CH:5](C(OCC)=O)[C:6]([O:8]CC)=[O:7].Cl>C(O)(=O)C>[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19388169Diethyl [(2-fluorophenyl)methyl]propanedioate

Product 1

HCID 20638663-(2-Fluorophenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

49 g (0.183 mol) of diethyl 2-(2-fluorobenzyl)malonate were mixed with 183 ml of 37% HCl and 9.4 ml of glacial acetic acid. The mixture was heated atreflux for 27 hours, then cooled; the solid precipitated was filtered, taken up with water, basified with sat. NaHCO3, washed with diethyl ether, then reacidified with 20% HCl, extracted with diethyl ether and washed with brine. After drying and evaporation, the oily residue was taken up with petroleum ether: upon freezing a white solid precipitated (21.5 g; 70%).

Workup

  1. temperatureThe mixture was heated atreflux for 27 hours
  2. temperaturecooled
  3. customthe solid precipitated
  4. filtrationwas filtered
  5. washwashed with diethyl ether
  6. extractionextracted with diethyl ether
  7. washwashed with brine
  8. customAfter drying
  9. customevaporation
  10. customprecipitated (21.5 g; 70%)

Sources & evidence

ORD record
ord-06b57fa83cc14910b674e9c84385a3ba
Source dataset
uspto-grants-1995_08
Patent number
US05446066

Reaction notes

Loading…