Hydrochloric Acid → 4-{2,6-Dichloro-4-[(3,3-dichloroprop-2-EN-1-YL)oxy]phenoxy}butan-1-OL

HRID 2234818Notes

Reaction equation

HRID 2234818 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([Cl:16])=[CH:14][C:13]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])=[CH:12][C:11]=1[Cl:23])(=O)C.[OH-].[Na+].O.Cl>CO>[Cl:22][C:20]([Cl:21])=[CH:19][CH2:18][O:17][C:13]1[CH:12]=[C:11]([Cl:23])[C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])=[C:15]([Cl:16])[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 184295004-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]butyl acetate

Product 1

HCID 222571304-{2,6-Dichloro-4-[(3,3-dichloroprop-2-EN-1-YL)oxy]phenoxy}butan-1-OLYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Twenty seven grams (0.067 mole) of 4-[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]butyl acetate was stirred and a solution of 5.4 grams (0.134 mole) of sodium hydroxide in 300 mL of methanol was added portion-wise. Upon completion of addition the reaction mixture was stirred at ambient temperature during a two hour period. After this time the reaction mixture was stirred with 400 mL of water and was neutralized with concentrated hydrochloric acid. The neutral mixture was extracted with four 150 mL portions of diethyl ether, and the combined extracted were washed with one 150 mL portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to a residue, yielding 22.5 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. extractionThe neutral mixture was extracted with four 150 mL portions of diethyl ether
  3. extractionthe combined extracted
  4. washwere washed with one 150 mL portion of an aqueous solution saturated with sodium chloride
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure to a residue

Sources & evidence

ORD record
ord-e4dc4f2e3740473c81c5b18781747f7a
Source dataset
uspto-grants-2010_05
Patent number
US07713970B2

Reaction notes

Loading…