Sodium Hydroxide → HCID 12940617, compound

HRID 1902810Notes

Reaction equation

HRID 1902810 reaction equation
C([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.[OH-].[Na+]>C(O)C>[I:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:13]2[CH:14]=[CH:15][C:10]([OH:9])=[CH:11][CH:12]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20513713HCID 20513713, compound

Product 1

HCID 12940617HCID 12940617, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

300 g of p-(p-iodophenoxy)phenyl benzoate are suspended in 2800 ml of 96% ethanol, treated with 700 g of 20% sodium hydroxide solution and heated on a boiling water-bath for 90 minutes. Subsequently, the alcohol is distilled off as an azeotropic mixture and the residue is treated with 1500 ml of deionized water. After the addition of 380 ml of concentrated hydrochloric acid, the mixture is extracted three times with 1500 ml of dichloromethane each time. The dichloromethane extract is washed twice with 500 ml of saturated sodium hydrogen carbonate solution, twice with 500 ml of 2 N hydrochloric acid and twice with 500 ml of water. After drying over sodium sulphate, the solution is evaporated to 500 ml under reduced pressure and 500 ml of hot n-hexane is added to the mixture. 201 g of p-(p-iodophenoxy)phenol melting point 119° C.-121° C. is obtained.

Workup

  1. temperatureheated on a boiling water-bath for 90 minutes
  2. distillationSubsequently, the alcohol is distilled off as an azeotropic mixture
  3. additionthe residue is treated with 1500 ml of deionized water
  4. additionAfter the addition of 380 ml of concentrated hydrochloric acid
  5. extractionthe mixture is extracted three times with 1500 ml of dichloromethane each time
  6. extractionThe dichloromethane extract
  7. washis washed twice with 500 ml of saturated sodium hydrogen carbonate solution, twice with 500 ml of 2 N hydrochloric acid and twice with 500 ml of water
  8. dry with materialAfter drying over sodium sulphate
  9. customthe solution is evaporated to 500 ml under reduced pressure and 500 ml of hot n-hexane
  10. additionis added to the mixture

Sources & evidence

ORD record
ord-49e8f9ee36eb4eb2a6b9f48fc4d9e1b6
Source dataset
uspto-grants-1982_12
Patent number
US04365991

Reaction notes

Loading…