Hydrochloric Acid → (1,1'-Biphenyl)-2,3'-diol

HRID 483857

Reaction equation

HRID 483857 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(S)CCC.C[CH:14]1[CH2:20][C:19](C)(C)[CH2:18][C:16](=[O:17])[CH2:15]1.Cl.[OH-].[Na+]>O>[CH:20]1[CH:19]=[C:18]([C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([OH:7])[CH:2]=2)[C:16]([OH:17])=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 8012ButanethiolHCID 133983,3,5-TrimethylcyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 33665(1,1'-Biphenyl)-2,3'-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

564 (6 mol) of phenol, 10.8 g (0.12 mol) of butanethiol and 140 g (1 mol) of dihydroisophorone (3,3,5-trimethylcyclohexan-1-one) are introduced into a stirring apparatus equipped with a stirrer, thermometer, reflux condenser and gas inlet pipe at 30° C. At this temperature 44 g of 37% HCl are added. The reaction mixture is stirred for about 70 h at 28°-30° C. When 95% of the ketone has been converted (examined by GC) 2 l of water are added to the reaction mixture and a pH value of 6 is adjusted by adding a 45% NaOH solution. The reaction mixture is stirred for one hour at 80° C. and is then cooled to 25° C. The aqueous phase is decanted off and the remaining residue is washed with water at 80° C. The resulting crude product is filtered off and hot-extracted twice with n-hexane and twice with toluene and then filtered at 30° C.

Workup

  1. customequipped with a stirrer
  2. additionare added to the reaction mixture
  3. stirringThe reaction mixture is stirred for one hour at 80° C.
  4. temperatureis then cooled to 25° C
  5. customThe aqueous phase is decanted off
  6. washthe remaining residue is washed with water at 80° C
  7. filtrationThe resulting crude product is filtered off
  8. extractionhot-extracted twice with n-hexane and twice with toluene
  9. filtrationfiltered at 30° C.

Sources & evidence

ORD record
ord-a67468e662174048a3906393fdd81dc1
Source dataset
uspto-grants-1993_07
Patent number
US05227458

Linked notes

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