Hydrochloric Acid → 4-[(2-Fluorobenzyl)oxy]benzoic acid

HRID 410000Notes

Reaction equation

HRID 410000 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1.[OH-].[K+].Cl>CO.C1COCC1>[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19861855Methyl 4-[(2-fluorophenyl)methoxy]benzoate

Product 1

HCID 64628464-[(2-Fluorobenzyl)oxy]benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(2-fluorobenzyloxy)benzoate (P1, 10.0 g, 26.9 mmol) was dissolved in methanol (60 mL) and THF (90 mL). A 45 wt % potassium hydroxide solution (20 mL) was then added and the resulting exotherm was controlled by a water bath. After 1.5 days at 20-25° C. the solution became a thick suspension. Using a water bath to control the exotherm, 20 mL of concentrated HCl was added. The mixture was then concentrated to remove the THF and methanol and 150 mL water was added. The solid was isolated by filtration and washed with 50 mL water. After drying under vacuum, the title compound was isolated as a white crystalline solid (9.4 g, 99% yield).

Workup

  1. customthe resulting exotherm was controlled by a water bath
  2. additionwas added
  3. concentrationThe mixture was then concentrated
  4. customto remove the THF and methanol and 150 mL water
  5. additionwas added
  6. customThe solid was isolated by filtration
  7. washwashed with 50 mL water
  8. customAfter drying under vacuum

Sources & evidence

ORD record
ord-ca2733eec1d54aea9fcfe32777919684
Source dataset
uspto-grants-2014_06
Patent number
US08759542B2

Reaction notes

Loading…