Nitrogen → (1,1'-Biphenyl)-2,2'-diol

HRID 1154752Notes

Reaction equation

HRID 1154752 reaction equation
[OH-:1].[Na+].Br[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.N#N.[OH2:19]>>[C:8]1([OH:19])[C:7]([C:10]2[C:15]([OH:1])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][CH:9]=1

Participants

5

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 71104,4'-DibromobiphenylHCID 14798Sodium Hydroxide

Product 1

HCID 15731(1,1'-Biphenyl)-2,2'-diol

Conditions

Temperature
300 °C

Procedure

A 600 ml autoclave was charged with 400 ml of 1N NaOH (0.4 mole), 11.5 g (37 mmole) 4,4'-dibromobiphenyl and 64 mg (0.256 mmole) CuSO4.5H2O as 4 ml of 0.064M solution in H2O. The autoclave was pressure checked with N2 to 1100 psi, vented, flushed with air and resealed. The autoclave was heated to 300° C. at an autogenic pressure of 1168 psi. These conditions were maintained for two hours. After cooling and venting the aqueous reaction product was filtered to remove a grey solid which probably contained catalyst and unreacted starting material. This filter was then removed to a second filter flask. Any starting material remaining was recovered by washing with acetone and stripping the solvent on a rotary evaporator. The filtered aqueous product solution was acidified (pH2) with 25% sulfuric acid. The precipitated crude biphenol (4,4'-dihydroxybiphenyl) was filtered and washed with water (50 ml).

Workup

  1. customflushed with air
  2. temperatureThese conditions were maintained for two hours
  3. temperatureAfter cooling
  4. filtrationwas filtered
  5. customto remove a grey solid which probably contained catalyst
  6. customThis filter was then removed to a second filter flask
  7. customAny starting material remaining was recovered
  8. washby washing with acetone
  9. customon a rotary evaporator
  10. customThe precipitated crude biphenol (4,4'-dihydroxybiphenyl)
  11. filtrationwas filtered
  12. washwashed with water (50 ml)

Sources & evidence

ORD record
ord-b59f667d8a9a412a973dbf0365d18a58
Source dataset
uspto-grants-1984_12
Patent number
US04490564

Reaction notes

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