Toluene → 4-(5-Phenyl-2-pyridylmethoxy)benzyl alcohol

HRID 349999Notes

Reaction equation

HRID 349999 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][OH:14])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=[O:16].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][O:14][C:22]3[CH:23]=[CH:24][C:19]([CH2:25][OH:16])=[CH:20][CH:21]=3)=[N:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 54044516(5-Phenylpyridin-2-yl)methanol

Product 1

HCID 694233514-(5-Phenyl-2-pyridylmethoxy)benzyl alcoholYield 86%

Conditions

Temperature
70 °C

Procedure

A mixture of 5-phenyl-2-pyridylmethanol (1.98 g), thionyl chloride (1.6 ml) and toluene (30 ml) was stirred at 70° C. for 2 hours. After the reaction mixture was concentrated, saturated aqueous sodium bicarbonate solution was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. A mixture of the residue, 4-hydroxybenzyl alcohol (1.37 g), potassium carbonate (3.18 g) and N,N-dimethylformamide (50 ml) was stirred at 80° C. overnight. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to obtain 4-(5-phenyl-2-pyridylmethoxy)benzyl alcohol (2.69 g, yield 86%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 159–160° C.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. additionsaturated aqueous sodium bicarbonate solution was added to the residue, which
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. additionA mixture of the residue, 4-hydroxybenzyl alcohol (1.37 g), potassium carbonate (3.18 g) and N,N-dimethylformamide (50 ml)
  8. stirringwas stirred at 80° C. overnight
  9. additionThe reaction mixture was poured into water, which
  10. extractionwas extracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-129e18525f8b4462bb935ff55008caa1
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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