Hydrochloric Acid → 4-(Benzyloxy)benzoic acid

HRID 325788Notes

Reaction equation

HRID 325788 reaction equation
C([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)C.C([O-])([O-])=O.[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C(O)C>[CH2:19]([O:11][C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:3])=[O:12])=[CH:10][CH:9]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 8434EthylparabenHCID 11430Potassium Carbonate

Product 1

HCID 738804-(Benzyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 132.5 g ethyl-4-hydroxybenzoate, 135 g K2CO3 and 110 ml benzyl chloride in 900 ml of ethanol was refluxed under stirring for 18 hrs. The mixture was warm filtered, and the filtrate evaporated. The residue was dissolved in 700 ml of water, 98 g of KOH was added, whereafter the mixture was refluxed with stirring for 2 hrs, or until a clear solution was obtained. The pH of the solution was adjusted to pH 1 with conc. HCl, and the crystalline material formed was filtered off. The identity of the product was confirmed with NMR.

Workup

  1. temperaturewas refluxed
  2. temperatureThe mixture was warm
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. dissolutionThe residue was dissolved in 700 ml of water
  6. addition98 g of KOH was added, whereafter the mixture
  7. temperaturewas refluxed
  8. stirringwith stirring for 2 hrs
  9. customuntil a clear solution was obtained
  10. customthe crystalline material formed
  11. filtrationwas filtered off

Sources & evidence

ORD record
ord-b2e946900a144925a2973e0efb6a33c8
Source dataset
uspto-grants-1984_04
Patent number
US04442300

Reaction notes

Loading…