Diphenic acid → (1,1'-Biphenyl)-2,2'-dimethanol

HRID 232437

Reaction equation

HRID 232437 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:16]2[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18](O)=[O:19])[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:9](O)=[O:10]>C1COCC1>[OH:10][CH2:9][C:8]1[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=1[C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[CH2:18][OH:19]

Participants

4

Reactant 2

HCID 10210Diphenic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 243265(1,1'-Biphenyl)-2,2'-dimethanolYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (12.60 grams, 0.332 mol) and THF (175 ml) were placed in a dry 500 ml three-necked round-bottomed flask fitted with a condenser, addition funnel, nitrogen inlet, and magnetic stirrer. The mixture was cooled with an ice bath and diphenic acid (40.00 grams, 0.165 mol) in THF (100 ml) was added dropwise to the stirring mixture. After the addition was complete, the flask was removed from the ice bath and allowed to warm to room temperature. The reaction mixture was heated at reflux for 2 hours, then stirred overnight at room temperature. After cooling the mixture with an ice bath, water (12.6 ml) was added dropwise, followed by the successive dropwise addition of 15% aqueous sodium hydroxide (12.6 ml) and water (38 ml). The resulting yellow mixture was warmed to room temperature, and the solids were separated by vacuum filtration. The filtrate was placed on a rotary evaporator to remove the solvent. The remaining brownish-yellow solid was recystallized from toluene-hexane to give 28.60 grams (81% yield) of light brown solid product, melting point 105° to 108° C. 1H NMR (CDCl3): δ 2.77 (br s, 2H, --OH); 3.95 (s, 4H, --CH2 --); 6.50-7.25 (m, 8H, aromatic).

Workup

  1. customfitted with a condenser, addition funnel, nitrogen inlet, and magnetic stirrer
  2. temperatureThe mixture was cooled with an ice bath
  3. additionAfter the addition
  4. customthe flask was removed from the ice bath
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux for 2 hours
  7. temperatureAfter cooling the mixture with an ice bath
  8. additionwater (12.6 ml) was added dropwise
  9. additionfollowed by the successive dropwise addition of 15% aqueous sodium hydroxide (12.6 ml) and water (38 ml)
  10. temperatureThe resulting yellow mixture was warmed to room temperature
  11. customthe solids were separated by vacuum filtration
  12. customThe filtrate was placed on a rotary evaporator
  13. customto remove the solvent
  14. customto give 28.60 grams (81% yield) of light brown solid product, melting point 105° to 108° C

Sources & evidence

ORD record
ord-061558fd945f460986ec9256b4ae57f2
Source dataset
uspto-grants-1989_07
Patent number
US04851581

Linked notes

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