Potassium Iodide → HCID 15679048, compound

HRID 1111273Notes

Reaction equation

HRID 1111273 reaction equation
[CH3:1][C:2]1[C:3]([OH:16])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH:26](Cl)[C:27]([OH:29])=[O:28]>CC(O)C>[CH3:1][C:2]1[C:3]2[O:16][CH:26]([C:27]([OH:29])=[O:28])[O:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6597Dichloroacetic Acid2×HCID 11430Potassium CarbonateHCID 12414461HCID 12414461, compound

Product 1

HCID 15679048HCID 15679048, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(3-Methyl-2-hydroxyphenyl)(2-hydroxyphenyl)-methane (3.4 g, 16 mmol), potassium carbonate (8.84 g, 64 mmol), potassium iodide (0.53 g, 3.2 mmol), dichloroacetic acid (2.06 g, 16 mmol), and 65 ml of 2-propanol were heated at reflux with stirring under nitrogen for 30 hours. Another 2.05 g (16 mmol) of dichloroacetic acid was added and heating at reflux continued for 60 hours. The 2-propanol was then removed by evaporation under reduced pressure and the residue was diluted with distilled water and acidified with 2N hydrochloric acid. This mixture was extracted with ether and the ether extract was dried over magnesium sulfate and evaporated under reduced pressure to obtain 1.8 g (42 percent of theory) of the title compound as a solid residue. A purified sample melting at 171° C. was obtained by recrystallization from a mixture of methylcyclohexane and acetone. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. temperatureat reflux
  2. temperatureheating
  3. temperatureat reflux
  4. waitcontinued for 60 hours
  5. customThe 2-propanol was then removed by evaporation under reduced pressure
  6. additionthe residue was diluted with distilled water
  7. extractionThis mixture was extracted with ether
  8. extractionthe ether extract
  9. dry with materialwas dried over magnesium sulfate
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8ea5223a7ab540268d31075018f073f4
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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