Hydrochloric Acid → 4-(4-Fluorophenyl)-4-hydroxybutanoic acid

HRID 27913Notes

Reaction equation

HRID 27913 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][C:11](=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:14].[Na+].Cl>O>[OH:13][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH2:9][CH2:10][C:11]([OH:12])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 103541gamma-(4-Fluorophenyl)-gamma-butyrolactone

Product 1

HCID 64847754-(4-Fluorophenyl)-4-hydroxybutanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Commercial γ-(p-fluorophenyl)-γ-butyrolactone, 18.0 g. (0.10 mole) was added to a solution of 14.0 g. (0.35 mole) of sodium hydroxide in 100 ml. of water and the mixture heated at reflux for 40 minutes. After cooling to 0° C., 70 ml of 6 N hydrochloric acid was added at 0°-15° C. for one hour. The white solid which formed was filtered, washed with pentane and air dried to afford racemic-4-hydroxy-4-(p-fluorophenyl)butyric acid, 18.43 g., (93% yield). When heated to temperatures of about 100° C., the hydroxy acid was converted back to the starting lactone.

Workup

  1. addition(0.10 mole) was added to a solution of 14.0 g
  2. temperatureat reflux for 40 minutes
  3. customThe white solid which formed
  4. filtrationwas filtered
  5. washwashed with pentane and air
  6. customdried

Sources & evidence

ORD record
ord-6a46657cf72947a78360c7769097fa78
Source dataset
uspto-grants-1980_09
Patent number
US04224329

Reaction notes

Loading…