Hydrochloric Acid → HCID 54361008, compound

HRID 2305072Notes

Reaction equation

HRID 2305072 reaction equation
[C:1]([O:5][N:6]=[C:7]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([O:24]C(=O)C2C=CC=CC=2)=[CH:19][C:18]=1[Cl:33])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>CO.O>[C:1]([O:5][N:6]=[C:7]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[C:18]([Cl:33])=[CH:19][C:20]([OH:24])=[CH:21][C:22]=1[Cl:23])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54363885HCID 54363885, compound

Product 1

HCID 54361008HCID 54361008, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.99 g of 5-(2,6-dichloro-4-(benzoyloxy)phenoxy)-pentyloxyacetone O-tert-butyloxime dissolved in 7.5 ml of methanol is added a solution of 0.15 g of potassium hydroxide dissolved in 1.5 ml of water. After stirring at room temperature for 1 hour, the reaction mixture is acidified by the addition of diluted hydrochloric acid, and concentrated. Water is added to the residue, and the mixture is extracted twice with ethyl acetate. The ethyl acetate layers are combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product is subjected to silica gel chromatography, which affords 5-(2,6-di-chloro-4-hydroxyphenoxy)pentyloxyacetone O-tert-butyloxime.

Workup

  1. concentrationconcentrated
  2. additionWater is added to the residue
  3. extractionthe mixture is extracted twice with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a crude product

Sources & evidence

ORD record
ord-3ec7f45196404ac8a8bea7e16e77d040
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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