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

HRID 363103Notes

Reaction equation

HRID 363103 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, to which 33 g of 30% potassium hydroxide 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 150 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 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 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-69cc213fb3d548778104098f232661d9
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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