Hydrochloric Acid → HCID 117964237, compound

HRID 511900Notes

Reaction equation

HRID 511900 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:9](S)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:22]1(=[O:28])[CH2:27][CH2:26][CH2:25][CH:24]=[CH:23]1.[OH-:29].[Na+]>CO>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([C:10]2([C:25]3[CH:26]=[CH:27][C:22]([OH:28])=[CH:23][CH:24]=3)[CH2:11][CH2:12][CH2:13][CH:14]([C:15]3[CH:20]=[CH:19][C:18]([OH:29])=[CH:17][CH:16]=3)[CH2:9]2)=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 81951-DodecanethiolHCID 135942-Cyclohexen-1-oneHCID 14798Sodium Hydroxide

Product 1

HCID 117964237HCID 117964237, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

1412 g of phenol, 78.2 g of 35% hydrochloric acid, 15.2 g of dodecyl mercaptan, and 144 g of methanol were introduced to a 4-way flask of 3 liters in capacity, into which 144 g of 2-cyclohexene-1-one was dripped over 10 hours in a nitrogen ambience with the liquid temperature kept at 30 to 32° C., at the end of which the mixture was agitated for 46 hours at 30° C. After the end of reaction, aqueous sodium hydroxide solution was added to neutralize the liquid, which was then heated to distill out the methanol. Thereafter, the water layer was separated and removed and the obtained oil layer was mixed with water and methyl isobutyl ketone, after which the mixture was agitated and water-washed to separate and remove the water layer. From the obtained oil layer, the methyl isobutyl ketone and unreacted phenol were distilled out under reduced pressure and removed. Toluene was added to the residue and the separated crystal was filtered out at room temperature and then dried to obtain a crude crystal of 1,1,3-tris(4-hydroxyphenyl)cyclohexane of 95% purity (according to the high-speed liquid chromatography).

Workup

  1. customkept at 30 to 32° C., at the end of which
  2. additionwas added
  3. temperaturewas then heated
  4. distillationto distill out the methanol
  5. customThereafter, the water layer was separated
  6. customremoved
  7. additionthe obtained oil layer was mixed with water and methyl isobutyl ketone
  8. stirringafter which the mixture was agitated
  9. washwater-washed
  10. customto separate
  11. customremove the water layer
  12. distillationFrom the obtained oil layer, the methyl isobutyl ketone and unreacted phenol were distilled out under reduced pressure
  13. customremoved
  14. additionToluene was added to the residue
  15. filtrationthe separated crystal was filtered out at room temperature
  16. customdried

Sources & evidence

ORD record
ord-04af32d1f9024293b5f90eb371c8f66d
Source dataset
uspto-grants-2015_08
Patent number
US09102596B2

Reaction notes

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