Hydrochloric Acid → HCID 178447845, compound

HRID 465288

Reaction equation

HRID 465288 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl.O>C1(C)C=CC=CC=1>[OH:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2([C:20]3[CH:21]=[CH:22][C:17]([OH:23])=[CH:18][CH:19]=3)[CH2:6][CH2:5][CH:4]([C@H:1]3[CH2:3][CH2:2][C@H:1]([CH2:4][CH2:5][CH3:6])[CH2:3][CH2:2]3)[CH2:9][CH2:8]2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 996PhenolHCID 178447904HCID 178447904, compound

Product 1

HCID 178447845HCID 178447845, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(Trans-4-n-propylcyclohexyl)cyclohexanone (449 g), phenol (756 g) and CaCl (446 g) were mixed, followed by gradually dropwise adding conc. hydrochloric acid (335 ml) with vigorous stirring at room temperature, further agitating the mixture for 30 minutes after completion of the dropwise addition, allowing the resulting material to stand at room temperature, further for 50 hours, adding hot water (2 l) and toluene (3 l), heating the mixture, cooling, filtering off crystals, washing the crystals with water and then with toluene, drying the crystals and recrystallizing from tetrahydrofuran solvent to obtain white crystals of 1,1-bis(4-hydroxyphenyl)-4-(trans-4-n-propylcyclohexyl)cyclohexane as a diol compound of the present invention (436 g). M.P.: 222.0°-222.8° C.

Workup

  1. stirringfurther agitating the mixture for 30 minutes
  2. additionafter completion of the dropwise addition
  3. temperatureheating the mixture
  4. temperaturecooling
  5. filtrationfiltering off crystals
  6. washwashing the crystals with water
  7. dry with materialwith toluene, drying the crystals
  8. customrecrystallizing from tetrahydrofuran solvent

Sources & evidence

ORD record
ord-e28bd19730d147eda8d50ce302c07b73
Source dataset
uspto-grants-1992_10
Patent number
US05152918

Linked notes

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