Hydrochloric Acid → HCID 67591893, compound

HRID 862139Notes

Reaction equation

HRID 862139 reaction equation
OC[C:3]1[CH:8]=[C:7]([C:9]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:10])[CH:6]=[C:5](CO)[C:4]=1[OH:19].[C:20]1([CH:27]=[CH:26][CH:25]=[C:23]([OH:24])[CH:22]=1)[OH:21].C1(C)C=CC=CC=1.Cl>O>[C:9]([C:7]1[CH:8]=[CH:3][C:4]([OH:19])=[CH:5][CH:6]=1)([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:10])[CH3:11].[C:20]1([CH:27]=[CH:26][CH:25]=[C:23]([OH:24])[CH:22]=1)[OH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 5054ResorcinolHCID 11065384HCID 11065384, compound

Product 1

HCID 67591893HCID 67591893, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a four-necked flask equipped with a fractionator and a thermometer were placed 66.5 g (0.25 mole) of 2,6-bis(hydroxymethyl)-4-t-octylphenol (purity: 99.1%) synthesized in the same manner as in the former half of Example 8, 82.5 g (0.75 mole) of resorcin and 100 ml of toluene, and 36% hydrochloric acid was added thereto so that the pH became 4, after which the temperature was elevated to 112° C. and then kept at that temperature for two hours while the water formed and toluene were removed by azeotropic distillation. The temperature was elevated to 150° C. and the reaction mixture was concentrated at a reduced pressure of 50 mmHg for one hour and then cooled to 80° C., after which 200 ml of toluene and 200 ml of water were added thereto to wash the mixture. The mixture was then allowed to stand to separate it into two layers. The upper layer (toluene solution) was transferred to a still, and then heated to 180° C., at which temperature the toluene solution was distilled at 3 mmHg for two hours to remove the toluene and unreacted resorcin, thereby obtaining a resorcin p-t-octylphenol resin [I].

Workup

  1. customIn a four-necked flask equipped with a fractionator
  2. additionwas added
  3. customwas elevated to 112° C.
  4. customformed
  5. customtoluene were removed by azeotropic distillation
  6. customwas elevated to 150° C.
  7. concentrationthe reaction mixture was concentrated at a reduced pressure of 50 mmHg for one hour
  8. additionafter which 200 ml of toluene and 200 ml of water were added
  9. washto wash the mixture
  10. customto separate it into two layers
  11. temperaturethen heated to 180° C., at which temperature the toluene solution
  12. distillationwas distilled at 3 mmHg for two hours
  13. customto remove the toluene and unreacted resorcin

Sources & evidence

ORD record
ord-5c3ebc96dd1b4d32a92b5e75c694bcb2
Source dataset
uspto-grants-1998_02
Patent number
US05717053

Reaction notes

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