Hydrochloric Acid → HCID 178444399, compound

HRID 344835Notes

Reaction equation

HRID 344835 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[Ca+2].[Cl-].Cl>C(OCC)(=O)C.O>[OH:27][C:21]1[CH:26]=[CH:25][C:24]([C:17]2([C:24]3[CH:25]=[CH:26][C:21]([OH:27])=[CH:22][CH:23]=3)[CH2:18][CH2:19][CH:14]([CH2:13][CH2:12][C@H:9]3[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]3)[CH2:15][CH2:16]2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 5284359Calcium ChlorideHCID 178444416HCID 178444416, compound

Product 1

HCID 178444399HCID 178444399, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[2-(Trans-4-n-pentylcyclohexyl)ethyl]cyclohexanone (112.4 g), phenol (152.7 g) and calcium chloride (90.1 g) were mixed, followed by gradually dropwise adding conc. hydrochloric acid (68 ml) with vigorous stirring at room temperature, agitating the mixture for 30 minutes after completion of the dropwise addition, further allowing the resulting material to stand at room temperature for 24 hours, adding hot water (0.5 l) and ethyl acetate (2 l) to dissolve it on heating, washing with saturated NaCl aqueous solution using hot water at 40° to 50° C., drying over Na2SO4, filtering, concentrating and recrystallizing the resulting concentrate from a mixed solvent of ethyl alcohol and methyl alcohol (87:13) (SOLMIX® made by Nihon Kasei Co., Ltd.) to obtain white crystals of 1,1-bis(4-hydroxyphenyl)-4-[2-(trans-4-n-pentylcyclohexyl)ethyl]cyclohexane (78.8 g) as a diol compound of the present invention. M.P.: 203.4-204.4° C.

Workup

  1. stirringagitating the mixture for 30 minutes
  2. additionafter completion of the dropwise addition
  3. dissolutionto dissolve it
  4. temperatureon heating
  5. washwashing with saturated NaCl aqueous solution
  6. customat 40° to 50° C.
  7. dry with materialdrying over Na2SO4
  8. filtrationfiltering
  9. concentrationconcentrating
  10. customrecrystallizing the resulting
  11. concentrationconcentrate from a mixed solvent of ethyl alcohol and methyl alcohol (87:13) (SOLMIX® made by Nihon Kasei Co., Ltd.)

Sources & evidence

ORD record
ord-731ccca7d58c41df89e80a3cc66ed1bd
Source dataset
uspto-grants-1991_10
Patent number
US05053544

Reaction notes

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