4-Hydroxybenzoic Acid → 4-[(4-chlorobenzyl)oxy]benzoic acid

HRID 1079103Notes

Reaction equation

HRID 1079103 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.O>CN(C)C=O>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 22728543Water ethylacetate

Product 1

HCID 9616084-[(4-chlorobenzyl)oxy]benzoic acidYield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 10 g of 4-hydroxybenzoic acid in 100 ml of N,N-dimethylformamide were added 29.1 g of 4-chlorobenzyl chloride and 25 g of potassium carbonate. The mixture was stirred at 60° C. for 3 hours. After cooling, the reaction mixture was treated with ethyl acetate-water. The resulting ethyl acetate layer was separated, washed with water, dried with anhydrous magnesium sulfate, and subjected to vacuum distillation to remove the solvent. The resulting residue was washed with n-hexane, then collected by filtration, and suspended in 50 ml of ethanol. To the suspension was added 100 ml of a 2N aqueous sodium hydroxide solution. The mixture was stirred at room temperature for 4 days and then neutralized with concentrated hydrochloric acid. The resulting crystals were collected by filtration and recrystallized from chloroform to obtain 16.7 g of 4-(4-chlorobenzyloxy)benzoic acid.

Workup

  1. temperatureAfter cooling
  2. customThe resulting ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationsubjected to vacuum distillation
  6. customto remove the solvent
  7. washThe resulting residue was washed with n-hexane
  8. filtrationcollected by filtration
  9. additionTo the suspension was added 100 ml of a 2N aqueous sodium hydroxide solution
  10. stirringThe mixture was stirred at room temperature for 4 days
  11. filtrationThe resulting crystals were collected by filtration
  12. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-2e5769d3c1534b92ad3060e5fca6097b
Source dataset
uspto-grants-1996_08
Patent number
US05550292

Reaction notes

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