Hydrochloric Acid → [1,1'-Biphenyl]-3-methanol, 2-methyl-

HRID 485537

Reaction equation

HRID 485537 reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[ClH:13].[OH-].[K+]>[Fe].C(O)C>[CH3:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:6][CH:7]=[CH:8][C:9]=1[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:3]=1.[ClH:13].[OH:5][CH2:4][C:3]1[C:2]([CH3:1])=[C:9]([CH:8]=[CH:7][CH:6]=1)[NH2:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 902892-Methyl-3-nitrobenzyl alcohol

Product 2

HCID 596875[1,1'-Biphenyl]-3-methanol, 2-methyl-HCID 20270659(3-Amino-2-methylphenyl)methanol hydrochloride

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

2-Methyl[1,1'-biphenyl]-3-methanol was prepared as follows: To 100 ml of stirred 50% aqueous ethanol was added 2-methyl-3-nitrobenzyl alcohol (41.8 g, 0.25 mole) and 85.0 grams of iron powder. The mixture was brought to reflux, and 5.2 ml of concentrated hydrochloric acid was slowly added. Upon complete addition, the reaction mixture was stirred under reflux for 2 hours. The reaction mixture was then made just basic with ethanolic 15% potassium hydroxide. The hot mixture was filtered through diatomaceous earth to remove the iron. The filter cake was washed with ethanol. The filtrate was acidified with hydrogen chloride, then allowed to stand at room temperature for 16 hours. The ethanol was removed by evaporation under reduced pressure. Hexane was added to the residue, and the water-hexane azeotrope was removed by distillation. The addition of hexane and the subsequent removal of the water-hexane azeotrope by distillation was repeated three times. The 3-hydroxymethyl-2-methylaniline hydrochloride residue thus obtained was used as follows.

Workup

  1. temperatureto reflux
  2. additionUpon complete addition
  3. temperatureunder reflux for 2 hours
  4. filtrationThe hot mixture was filtered through diatomaceous earth
  5. customto remove the iron
  6. washThe filter cake was washed with ethanol
  7. customThe ethanol was removed by evaporation under reduced pressure
  8. additionHexane was added to the residue
  9. customthe water-hexane azeotrope was removed by distillation
  10. additionThe addition of hexane
  11. customthe subsequent removal of the water-hexane azeotrope
  12. distillationby distillation

Sources & evidence

ORD record
ord-76443db8337b40b1b4d9d33e6988402c
Source dataset
uspto-grants-1985_08
Patent number
US04536591

Linked notes

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