Hydrochloric Acid → 4-(4-Hydroxyphenyl)-3-cyclohexen-1-ol

HRID 330109Notes

Reaction equation

HRID 330109 reaction equation
C1(O)C=CC=CC=1.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(C3C=CC(O)=CC=3)[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.CN1CCN(C)C1=O.[OH-].[Na+].Cl>O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 996Phenol2×HCID 66611,3-Dimethyl-2-imidazolidinone2×HCID 14798Sodium HydroxideHCID 10731776Phenol, 4,4'-(4-hydroxycyclohexylidene)bis-

Product 1

HCID 143657084-(4-Hydroxyphenyl)-3-cyclohexen-1-olYield 69.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The phenol adducts of 4,4-bis(4-hydroxyphenyl) cyclohexanol obtained as described above were reacted in toto in a manner similar to that described in Example 1 of Japanese Patent Application No. 89890/1987. Namely, the phenol adducts of 4,4-bis(4-hydroxyphenyl)cyclohexanol were added as a whole to a mixture of 100 ml of 1,3-dimethyl-2-imidazolidinone and 1 ml of a 50% aqueous solution of caustic soda. They were then reacted at 200°-220° C. for 3 hours. In the course of the reaction, the reaction system was depressurized after an elapsed time of 0.5 hour so as to draw phenol-containing 1,3-dimethyl-2-imidazolidinone out of the system. After completion of the reaction, the residue in the reaction tank was dissolved in caustic water and then acidified with hydrochloric acid to precipitate crystals. The crystals were collected by filtration, washed with water, dried under reduced pressure and then recrystallized from acetonitrile, thereby obtaining 22.3 g of 4-(4-hydroxyphenyl)-3-cyclohexen-1-ol. Purity: 99.1%. Purity-converted yield: 69.3% based on 4,4-bis(4-hydroxyphenyl)cyclohexanol.

Workup

  1. customabove were reacted in toto in a manner similar to
  2. customThey were then reacted at 200°-220° C. for 3 hours
  3. customIn the course of the reaction
  4. customafter an elapsed time of 0.5 hour
  5. customAfter completion of the reaction
  6. customto precipitate crystals
  7. filtrationThe crystals were collected by filtration
  8. washwashed with water
  9. customdried under reduced pressure
  10. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-b53fb1a6c4c34e0dbdd8e42224def687
Source dataset
uspto-grants-1990_01
Patent number
US04894487

Reaction notes

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