Potassium Iodide → Spiro(cyclopropane-1,12'(12'H)-dibenzo[d,g][1,3]dioxocin)-6'-carboxylic Acid

HRID 1460381Notes

Reaction equation

HRID 1460381 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH:27](Cl)[C:28]([OH:30])=[O:29]>C(O)(C)C>[CH:4]1[C:3]2[C:8]3([CH2:10][CH2:9]3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH:27]([C:28]([OH:30])=[O:29])[O:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6597Dichloroacetic Acid2×HCID 11430Potassium CarbonateHCID 148397051,1-Bis(2-hydroxyphenyl)cyclopropane

Product 1

HCID 14839706Spiro(cyclopropane-1,12'(12'H)-dibenzo[d,g][1,3]dioxocin)-6'-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An 18.5 g (0.082 mole) sample of unpurified 1,1-bis(2-hydroxyphenyl)cyclopropane was combined with 44.0 g (0.32 mole) of potassium carbonate, 2.0 g (0.012 mole) of potassium iodide, 8.0 ml of dichloroacetic acid, and 400 ml of isopropyl alcohol. The mixture was heated at reflux with stirring for 24 hours. Another 8.0 ml of dichloroacetic acid was added and the mixture heated at reflux with stirring for another 48 hours. The volatiles were then removed by evaporation under reduced pressure. The solid that remained was dissolved in 300 ml of water. The resulting solution was extracted with 500 ml of ether, acidified with concentrated hydrochloric acid (carefully due to foaming), and then extracted with three 500 ml portions of ether. The latter ether extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound in crude form as a solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. temperaturethe mixture heated
  4. temperatureat reflux
  5. stirringwith stirring for another 48 hours
  6. customThe volatiles were then removed by evaporation under reduced pressure
  7. dissolutionThe solid that remained was dissolved in 300 ml of water
  8. extractionThe resulting solution was extracted with 500 ml of ether
  9. extractionthen extracted with three 500 ml portions of ether
  10. dry with materialThe latter ether extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d993f5a1f10b42029c23b3fb02f2aa72
Source dataset
uspto-grants-1991_12
Patent number
US05071465

Reaction notes

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