Hydrochloric Acid → 4-(2-Chlorobenzyloxy)-3,5-dichlorophenol

HRID 363094Notes

Reaction equation

HRID 363094 reaction equation
C([O:9][C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[C:12]([Cl:26])[CH:11]=1)(=O)C1C=CC=CC=1.[OH-].[K+].Cl>CO>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][O:17][C:13]1[C:14]([Cl:16])=[CH:15][C:10]([OH:9])=[CH:11][C:12]=1[Cl:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 543524561-Benzoyloxy-4-(2-chlorobenzyloxy)-3,5-dichlorobenzene

Product 1

HCID 540958994-(2-Chlorobenzyloxy)-3,5-dichlorophenolYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2.87 g of 1-benzoyloxy-4-(2-chlorobenzyloxy)-3,5-dichlorobenzene and 100 ml of methanol was added dropwise 5.1 g of 10% (w/w) aqueous potassium hydroxide solution, while stirring at room temperature. After stirring at room temperature for 6 hours, the reaction mixture was made weakly acidic by the addition of 10% hydrochloric acid, and the methanol was removed by distillation under reduced pressure. The residue was extracted twice with 100 ml of ethyl acetate. The combined ether layer was washed with water, and dried with anhydrous magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 1.17 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenol (55% yield), m.p. 108.3° C.

Workup

  1. stirringAfter stirring at room temperature for 6 hours
  2. customthe methanol was removed by distillation under reduced pressure
  3. extractionThe residue was extracted twice with 100 ml of ethyl acetate
  4. washThe combined ether layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customfollowed by removal of the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-e71ef3b9e1514184ba8122a9fd7a60ca
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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