Potassium Iodide → HCID 22151952, compound

HRID 1111276Notes

Reaction equation

HRID 1111276 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](C)=[CH:4][C:3]=1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16].[C:17](=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH:26](Cl)[C:27]([OH:29])=[O:28]>CC(O)C>[CH3:17][C:15]1[C:10]2[CH2:9][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[O:1][CH:26]([C:27]([OH:29])=[O:28])[O:16][C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6597Dichloroacetic Acid2×HCID 11430Potassium CarbonateHCID 4438647HCID 4438647, compound

Product 1

HCID 22151952HCID 22151952, compoundYield 126.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2-Hydroxy-5-methylphenyl)(2-hydroxyphenyl)methane (1.66 g, 7.7 mmol) was combined with 2.07 g (15 mmol) of potassium carbonate, 0.56 g (3.4 mmol) of potassium iodide, 0.99 g (7.7 mmol) of dichloroacetic acid and 50 ml of 2-propanol and the mixture heated at reflux with stirring for 24 hours. Another 7.7 mmol of dichloroacetic acid was added and the reaction continued for 2 days. The volatiles were removed by evaporation under reduced pressure and water added. The mixture was acidified with 1N hydrochloric acid and extracted with ether. The ether extract was dried over magnesium sulfate and the ether removed by evaporation under reduced pressure to obtain 2.63 g of the title compound in impure form as a brown oil. The proton nmr spectrum was consistent with the presence of desired product. A sample of the title compound prepared by hydrolysis of the product of Example 7 with potassium hydroxide in an aqueous methanol mixture at ambient temperature overnight melted at 61° C. and had a proton nmr spectrum consistent with the assigned structure.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux
  3. waitthe reaction continued for 2 days
  4. customThe volatiles were removed by evaporation under reduced pressure and water
  5. additionadded
  6. extractionextracted with ether
  7. extractionThe ether extract
  8. dry with materialwas dried over magnesium sulfate
  9. customthe ether removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-f5baadb33e4342efaaeb0072d33f79cb
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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