Water → (1,1'-Biphenyl)-2,3'-diol

HRID 893780Notes

Reaction equation

HRID 893780 reaction equation
COC1C=CC(C(C2C=C[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19](=O)[C:20]4[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22]C=4)[CH:15]=3)C=2)=O)=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH2:35]>C1(C)C=CC=CC=1.[OH-].[Na+]>[CH:16]1[CH:15]=[C:14]([C:19]2[CH:20]=[CH:25][CH:24]=[C:23]([OH:26])[CH:22]=2)[C:13]([OH:35])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 198911242,6-Bis(4-methoxybenzoyl)naphthalene

Product 1

HCID 33665(1,1'-Biphenyl)-2,3'-diolYield 92.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A 2.5 liter sulfonation flask fitted with thermometer, stirrer, condenser and nitrogen inlet is charged with 153 g (0.39 g mol) of 2,6-bis(4-methoxybenzoyl)naphthalene in 1350 ml of toluene and, with stirring, 282.7 g (2.12 mol) of aluminium chloride are added in portions over 15 minutes at 8° C. The reaction mixture is stirred for 4 hours at 75° C., then cooled to room temperature, and charged into 10 liters of water with vigorous stirring. The resultant suspension is filtered and the residue is vacuum dried at 130° C., giving 142.4 g (99.9% of theory) of a brownish powder which melts at 307° C. 67 g of the crude product are dissolved warm in 320.1 g 5% aqueous sodium hydroxide, and the solution is dried over Hyflo (filter aid based on diatomaceous earth (kieselguhr)) and the clear filtrate is charged to 2 liters of water containing 39.5 g of 37% of hydrochloric acid. The precipitated product is filtered, washed with water and vacuum dried at 130° C., giving 62.3 g (92.8% of theory) of the desired diphenol. The product melts at 307° C.

Workup

  1. customA 2.5 liter sulfonation flask fitted with thermometer, stirrer, condenser and nitrogen inlet
  2. stirringThe reaction mixture is stirred for 4 hours at 75° C.
  3. filtrationThe resultant suspension is filtered
  4. customdried at 130° C.
  5. customgiving 142.4 g (99.9% of theory) of a brownish powder which melts at 307° C
  6. customthe solution is dried over Hyflo (filter aid based on diatomaceous earth (kieselguhr))
  7. additionthe clear filtrate is charged to 2 liters of water containing 39.5 g of 37% of hydrochloric acid
  8. filtrationThe precipitated product is filtered
  9. washwashed with water and vacuum
  10. customdried at 130° C.

Sources & evidence

ORD record
ord-606f40e7c9cd46c1acd69845240e7b01
Source dataset
uspto-grants-1992_06
Patent number
US05126427

Reaction notes

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