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

HRID 1356974Notes

Reaction equation

HRID 1356974 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 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 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-95420fb89dc0466e94aabf50785088f0
Source dataset
uspto-grants-2003_07
Patent number
US06589914B2

Reaction notes

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