Hydrochloric Acid → HCID 59234914, compound

HRID 1919760Notes

Reaction equation

HRID 1919760 reaction equation
[I-:1].[K+].[OH-].[K+].[F:5][C:6]([F:24])([F:23])[C:7]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)([O:12][CH2:13][O:14][CH3:15])[C:8]([F:11])([F:10])[F:9].Cl[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>CO>[F:5][C:6]([F:23])([F:24])[C:7]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([I:1])[CH:17]=1)([O:12][CH2:13][O:14][CH3:15])[C:8]([F:10])([F:9])[F:11]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 23665760Sodium HypochloriteHCID 87123106HCID 87123106, compound

Product 1

HCID 59234914HCID 59234914, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium iodide (1.24 g) and potassium hydroxide (0.46 g) were added to a mixed solution of 4-[1,1,1,3,3,3,-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]phenol (2.50 g, 8.21 mmol) in methanol (63 mL) at room temperature. Then, a 4% sodium hypochlorite solution (15.4 mL) was added in an ice bath over three hours. The mixture was returned to room temperature and stirred overnight. A 1 mol/L sodium thiosulfate aqueous solution was added to the reaction solution at room temperature, and then the pH was adjusted to 7 with 2 mol/L hydrochloric acid. After extraction with diethyl ether-water, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 2.44 g of the title compound (yield: 69%) as a colorless solid.

Workup

  1. customwas returned to room temperature
  2. extractionAfter extraction with diethyl ether-water
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-51563d5b7cc64d1fb5b441e1b001f5e3
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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