Potassium Hydroxide → 3-(2,6dichloro-4-(benzyloxy)phenoxy)-1-propyl alcohol

HRID 582341Notes

Reaction equation

HRID 582341 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[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][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[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 18504579HCID 18504579, compound

Product 1

HCID 120568873-(2,6dichloro-4-(benzyloxy)phenoxy)-1-propyl alcoholYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction vessel was charged with 3.75 g of 3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(benzyloxy)benzene, 5.0 g of 10% aqueous potassium hydroxide solution and 50 ml of methanol. After stirring at room temperature for 24 hours, the reaction mixture was concentrated. The concentrate was poured into water, and extracted twice with 150 m 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 2.56 g of 3-(2,6-dichloro-4-(benzyloxy)phenoxy)-1-propyl alcohol (90% yield).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe concentrate was poured into water
  3. extractionextracted twice with 150 m 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-20e6a1c105574b35a9474901193a7a77
Source dataset
uspto-grants-1999_07
Patent number
US05922880

Reaction notes

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