Potassium Hydroxide → 3-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-ol

HRID 363113Notes

Reaction equation

HRID 363113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:22][CH2:23][CH:24]=[C:25]([Cl:27])[Cl:26])[CH:5]=[C:6]([Cl:21])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12]C(=O)C1C=CC=CC=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([O:22][CH2:23][CH:24]=[C:25]([Cl:27])[Cl:26])[CH:5]=[C:6]([Cl:21])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][OH:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 184300283,5-Dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

Product 1

HCID 113139803-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-olYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction vessel was charged with 11.6 g of 3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 15.2 g of 10% aqueous potassium hydroxide solution and 300 ml of methanol. After stirring at room temperature for 24 hours, and the reaction mixture was concentrated. The concentrate was poured into water, and extracted twice with 150 ml of diethyl ether. 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 7.41 g of 3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propyl alcohol (83%o yield), m.p. 56.6° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe concentrate was poured into water
  3. extractionextracted twice with 150 ml of diethyl ether
  4. washThe combined ether layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto obtain a crude product

Sources & evidence

ORD record
ord-c74933b9e1f449039b5b4c2f1c7d13c4
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

Loading…