Hydrochloric Acid → HCID 13003958, compound

HRID 1439443Notes

Reaction equation

HRID 1439443 reaction equation
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])=[CH2:3]>C1(C)C=CC=CC=1.C1(O)C=CC=CC=1>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:2]([C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=2)([CH2:4][C:2]([C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=2)([CH3:4])[CH3:3])[CH3:3])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 584247p-Isopropenylphenol

Product 1

HCID 13003958HCID 13003958, compound

Reagents, catalysts & solvents 2

HCID 996PhenolSolventHCID 1140TolueneSolvent

Procedure

Hydrogen chloride is introduced for 6 hours at 0° C into a solution of 78.6 g (0.2 mol) of the bischlorocarbonic acid ester of dimeric p-isopropenylphenol prepared according to (a) in 180 ml of toluene and 150 g of phenol. The solvent and excess phenol are removed at reduced pressure and the reaction product is dissolved in 400 ml of methanol, and 200 ml of concentrated sodium hydroxide solution are added dropwise. The reaction mixture is then diluted with an equal quantity of water and heated to reflux. The methanol is distilled off, 400 ml of toluene are added and the tris-phenol is precipitated with dilute hydrochloric acid. The solvent phase is washed with water, dehydrated over sodium sulphate and concentrated by evaporation. After removal of the excess phenol by distillation, a small amount of bisphenol A distils over, which is followed by the tris-phenol fraction which distils over at 270°-280° C/0.05 Torr. Melting point 150°-151° C (from methylene chloride). Yield: 48 g = 66% of theoretical.

Workup

  1. customprepared
  2. customThe solvent and excess phenol are removed at reduced pressure
  3. dissolutionthe reaction product is dissolved in 400 ml of methanol
  4. addition200 ml of concentrated sodium hydroxide solution are added dropwise
  5. additionThe reaction mixture is then diluted with an equal quantity of water
  6. temperatureheated to reflux
  7. distillationThe methanol is distilled off
  8. addition400 ml of toluene are added
  9. customthe tris-phenol is precipitated with dilute hydrochloric acid
  10. washThe solvent phase is washed with water
  11. concentrationconcentrated by evaporation
  12. customAfter removal of the excess phenol
  13. distillationby distillation
  14. customa small amount of bisphenol A distils over, which
  15. customdistils over at 270°-280° C/0.05 Torr

Sources & evidence

ORD record
ord-f5d781a0498a4fd2bfe3308c4019fe81
Source dataset
uspto-grants-1977_11
Patent number
US04059638

Reaction notes

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