Thionyl Chloride → HCID 22903132, compound

HRID 1650638Notes

Reaction equation

HRID 1650638 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][C:14]=1[Cl:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[CH2:5]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([Cl:3])=[O:18])=[CH:15][C:14]=1[Cl:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 308481NSC210282

Product 1

HCID 22903132HCID 22903132, compound

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. customthe mixture was reacted
  2. temperatureunder reflux
  3. customreacted for 3 hours
  4. customwas removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a60e6aed6a4545d0b37880b9101c2a7e
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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