[1,1'-Biphenyl]-3,4-diol → HCID 20334219, compound

HRID 1706692Notes

Reaction equation

HRID 1706692 reaction equation
Br[CH:2]([CH2:8]Br)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:10]1([C:16]2[CH:17]=[C:18]([OH:23])[C:19](=[CH:21][CH:22]=2)[OH:20])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:10]1([C:16]2[CH:22]=[CH:21][C:19]3[O:20][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:8][O:23][C:18]=3[CH:17]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7075[1,1'-Biphenyl]-3,4-diolHCID 11430Potassium CarbonateHCID 97945Ethyl 2,3-dibromopropionate

Product 1

HCID 20334219HCID 20334219, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

46.1 g of ethyl 2,3-dibromopropionate was added slowly to a mixture of 30 g of 4-phenylcatechol, 66.2 g of potassium carbonate, and 250 ml of acetone. The mixture was refluxed for 18 hours, cooled and filtered. The solvent was evaporated from the filtrate under reduced pressure. The residue was extracted with hot cyclohexane. The extract was dried (MgSO4) and filtered. The solvent was evaporated from the filtrate under reduced pressure. The residue was taken up in hexane/methylene chloride. The solution was cooled. The resulting solid (7A) was separated and recrystallized from cyclohexane to give 7, mp: 103°-105° C.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solvent was evaporated from the filtrate under reduced pressure
  5. extractionThe residue was extracted with hot cyclohexane
  6. dry with materialThe extract was dried (MgSO4)
  7. filtrationfiltered
  8. customThe solvent was evaporated from the filtrate under reduced pressure
  9. temperatureThe solution was cooled
  10. customThe resulting solid (7A) was separated
  11. customrecrystallized from cyclohexane
  12. customto give 7, mp: 103°-105° C.

Sources & evidence

ORD record
ord-47efe6d6537a4ccc808acacabcff2411
Source dataset
uspto-grants-1980_06
Patent number
US04208424

Reaction notes

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