Hydrochloric Acid → 3,5-Dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenol

HRID 363092Notes

Reaction equation

HRID 363092 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][C:22]([F:25])=[C:21]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:20]=2)=[C:12]([Cl:33])[CH:11]=1)(=O)C1C=CC=CC=1.[OH-].[K+].Cl>CO>[Cl:16][C:14]1[CH:15]=[C:10]([OH:9])[CH:11]=[C:12]([Cl:33])[C:13]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 538852383,5-Dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenyl benzoate

Product 1

HCID 538576463,5-Dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenolYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction vessel was charged with 1.36 g of 3,5-dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenyl benzoate and 10 ml of methanol, to which 4.2 g of 10% potassium hydroxide solution was slowly added dropwise under ice cooling. After stirring for 1 hour, the reaction mixture was made weakly acidic by the addition of 10% hydrochloric acid, and extracted twice with 50 ml of diethyl ether under salting out. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.97 g of 3,5-dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenol (91% yield), m.p. 144.8° C.

Workup

  1. additionwas slowly added dropwise under ice cooling
  2. extractionextracted twice with 50 ml of diethyl ether under salting out
  3. washThe combined ether layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain a crude product

Sources & evidence

ORD record
ord-66ac54bfabd64052aed882d2116b4e8d
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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