Hydrochloric Acid → NSC210282

HRID 1650637Notes

Reaction equation

HRID 1650637 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11].[OH-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>CO.O1CCCC1.O>[CH2:14]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide2×HCID 198603-Chloro-4-hydroxybenzoic acid

Product 1

HCID 308481NSC210282

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixed solvent of methanol and tetrahydrofuran was dissolved 5.17 g of 4-hydroxy-3-chlorobenzoic acid, and a solution of 2.4 g of sodium hydroxide in 5 ml of water was added to the solution. Then, 10 ml of benzyl chloride was added to the mixture and the liquid was refluxed for 4 hours. Then, 1.2 g of sodium hydroxide was further added to the mixture, the liquid was refluxed for 2 hours, and the reaction liquid was put into 1N hydrochloric acid, and the precipitate was recovered by filtration, washed with water, methanol and n-pentane in succession and recrystallized from a mixed solvent of benzene and tetrahydrofuran to obtain 2.7 g of 4-benzyloxy-3-chlorobenzoic acid. Then, 15 g of thionyl chloride was added to 2.7 g of this 4-benzyloxy-3-chlorobenzoic acid, and the mixture was reacted under reflux and reacted for 3 hours. Unreacted thionyl chloride was removed by distillation under reduced pressure. Thus, 4-benzyloxy-3-chlorobenzoic acid chloride was quantitatively obtained.

Workup

  1. temperaturethe liquid was refluxed for 4 hours
  2. temperaturethe liquid was refluxed for 2 hours
  3. customthe reaction liquid
  4. filtrationthe precipitate was recovered by filtration
  5. washwashed with water, methanol and n-pentane in succession
  6. customrecrystallized from a mixed solvent of benzene and tetrahydrofuran

Sources & evidence

ORD record
ord-20432d0c880740408cebf2613c8d84e1
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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