Sodium Carbonate → 4,4"-Dihydroxyterphenyl

HRID 1085383Notes

Reaction equation

HRID 1085383 reaction equation
[OH-:1].[K+].[C:3](=[O:6])([O-])[O-].[Na+].[Na+].[C:9]1([C:23]2[C:24]([C:29]3[CH:34]=[CH:33]C=[CH:31][CH:30]=3)=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:14]=[CH:13][C:12](S(O)(=O)=O)(S(O)(=O)=O)[CH2:11][CH:10]=1>O>[OH:1][C:12]1[CH:13]=[CH:14][C:9]([C:23]2[C:24]([C:29]3[CH:34]=[CH:33][C:3]([OH:6])=[CH:31][CH:30]=3)=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 131716827Terphenyl-4,4-disulfonic acid

Product 1

HCID 225645284,4"-Dihydroxyterphenyl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
330 °C

Procedure

A 1-1 V2A stainless steel vessel equipped with a horseshoe stirrer was charged with 600 g of potassium hydroxide and 60 g of sodium carbonate, and 250 g of the crude product described under (a) were added at 300° C a little at a time over 2 hours. The temperature was raised to 330° C, and the contents were stirred for 3 hours. The contents were then cooled down in a controlled manner by addition of water, diluted with a total of 1.6 1 of water and filtered with suction. The residue was suspended in 2 l of water, and the suspension was acidified with concentrated hydrochloric acid, heated to 90° C and filtered with suction while still hot. The residue was dried and recrystallized from N,N-dimethylformamide. Purity (HPLC) 99.8%; yield: 102.0 g (74% based on terphenyl).

Workup

  1. additionwere added at 300° C a little at a time over 2 hours
  2. filtrationfiltered with suction
  3. temperatureheated to 90° C
  4. filtrationfiltered with suction while still hot
  5. customThe residue was dried
  6. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-f99ca2cbee4d40cdacbb9f240df6562c
Source dataset
uspto-grants-1991_04
Patent number
US05008472

Reaction notes

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