Hydrochloric Acid → 4-(3,3-Dichloro-2-propenyloxy)phenol

HRID 377713Notes

Reaction equation

HRID 377713 reaction equation
C([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]=[C:19]([Cl:21])[Cl:20])=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.[OH-].[K+].Cl>CO>[Cl:20][C:19]([Cl:21])=[CH:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([OH:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 185046614-(3,3-Dichloro-2-propenyloxy)phenyl benzoate

Product 1

HCID 111720144-(3,3-Dichloro-2-propenyloxy)phenolYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction vessel was charged with 44.1 g of 4-(3,3-dichloro-2-propenyloxy)phenyl benzoate and 400 ml of methanol, and 33 g of 30% aqueous potassium hydroxide solution was slowly added dropwise under ice cooling. After stirring for 1 hour, the mixture was made weak acidic by the addition of 10% hydrochloric acid, and then extracted twice with 150 m of diethyl ether under salting out. The ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 26.0 g of 4-(3,3-dichloro-2-propenyloxy)phenol (87% yield).

Workup

  1. additionwas slowly added dropwise under ice cooling
  2. extractionextracted twice with 150 m of diethyl ether under salting out
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give a crude product

Sources & evidence

ORD record
ord-7b4f819d25bd4534a34bf3959094fe69
Source dataset
uspto-grants-2000_02
Patent number
US06028100

Reaction notes

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