Hydrochloric Acid → 4,4'-Dihydroxybiphenyl

HRID 1649970Notes

Reaction equation

HRID 1649970 reaction equation
[OH-:1].[K+].[C:3](=[O:6])([O-])[O-].[Na+].[Na+].[C:9]1([C:19]2[CH:24]=[CH:23]C(S(O)(=O)=O)=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:12](S(O)(=O)=O)=[CH:11][CH:10]=1.Cl>O>[OH:1][C:12]1[CH:13]=[CH:14][C:9]([C:19]2[CH:24]=[CH:23][C:3]([OH:6])=[CH:21][CH:20]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 79202[1,1'-Biphenyl]-4,4'-disulfonic acid

Product 1

HCID 71124,4'-DihydroxybiphenylYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
320 °C

Procedure

400 g (6.1 moles) of potassium hydroxide having a water content of 15% by weight and 40 g (0.38 mole) of sodium carbonate were initially taken in a stirred 1 1 V2A stainless steel kettle and 195 g (0.5 mole) of the dipotassium salt of biphenyl-4,4'-disulfonic acid were introduced at 280° C. The temperature was then increased to 320° C., this temperature was maintained for 3 hours and the melt was cooled by constantly metering in water and simultaneously reducing the heating bath temperature. The reaction mixture was diluted with water and acidified with concentrated hydrochloric acid at 90° C. to a pH of 6.5. The resulting precipitate was filtered off under suction, and 4,4'-dihydroxybiphenyl was extracted by means of acetone. The extracting agent was removed to give 85.5 g (92%) of 4,4'-dihydroxybiphenyl, which had a purity of >99% (HPLC).

Workup

  1. additionwere introduced at 280° C
  2. temperaturethis temperature was maintained for 3 hours
  3. temperaturethe melt was cooled
  4. filtrationThe resulting precipitate was filtered off under suction, and 4,4'-dihydroxybiphenyl
  5. extractionwas extracted by means of acetone
  6. customThe extracting agent was removed

Sources & evidence

ORD record
ord-17644553494c467e8a3ecfe6183a56db
Source dataset
uspto-grants-1990_05
Patent number
US04922031

Reaction notes

Loading…