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

HRID 1030033Notes

Reaction equation

HRID 1030033 reaction equation
C[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].SCCC(O)=O.[CH3:16][CH:17]1CC(C)(C)[CH2:21][C:19](=[O:20])[CH2:18]1.Cl.[OH-].[Na+]>O>[CH:6]1[CH:5]=[C:4]([C:8]2[CH:16]=[CH:17][CH:18]=[C:19]([OH:20])[CH:21]=2)[C:3]([OH:9])=[CH:2][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 65143-Mercaptopropionic AcidHCID 113352,6-DimethylphenolHCID 133983,3,5-TrimethylcyclohexanoneHCID 14798Sodium Hydroxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

2196 g (18 mol) of 2,6-dimethylphenol, 38.2 g (0.36 mol) of β-mercaptopropionic acid and 420 g (3 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 35° C. Dry HCl gas is introduced into this solution at 35° C. over a period of 5 h. The mixture is then left to react at 28°-30° C. for a period of about 10 hours. When 95% of the ketone has been converted (examined by GC) 2.5 l of water are added to the reaction mixture and a pH value of 6 is adjusted by the addition of a 45% NaOH solution. The reaction mixture is stirred for one hour at 80° C. and then cooled to room temperature. The aqueous phase is decanted off and the remaining residue is washed with water at 60° C. The resulting crude product is filtered off and hot-extracted three times with n-hexane and is then filtered.

Workup

  1. customequipped with a stirrer
  2. waitThe mixture is then left
  3. customto react at 28°-30° C. for a period of about 10 hours
  4. additionare added to the reaction mixture
  5. temperaturecooled to room temperature
  6. customThe aqueous phase is decanted off
  7. washthe remaining residue is washed with water at 60° C
  8. filtrationThe resulting crude product is filtered off
  9. extractionhot-extracted three times with n-hexane
  10. filtrationis then filtered

Sources & evidence

ORD record
ord-69d37a585b8347ea80a5f2392a515fd2
Source dataset
uspto-grants-1992_04
Patent number
US05104723

Reaction notes

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