Benzhydrol → HCID 67057457, compound

HRID 1510204Notes

Reaction equation

HRID 1510204 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2].[CH:9]([OH:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[O-].[Na+]>Cl>[CH:9]([O:22][CH2:2][CH2:1][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7037BenzhydrolHCID 75024-VinylpyridineHCID 10942334Sodium Methoxide

Product 1

HCID 67057457HCID 67057457, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
135 °C

Procedure

With reference to FIG. 7, to a stirred solution of 4-vinylpyridine 1 (10 g, 95.1 mmol) and benzhydrol 2 (35.04 g, 190 mmol), was added sodium methoxide (1.541 g, 28.5 mmol). The reaction mixture was heated at 130-140° C. for 20 hrs, cooled to RT and acidified with 1 N HCl (150 ml). The solution was extracted with ethyl acetate (3×30 ml) to remove unreacted benzhydrol and side product dibenzhydryl ether. The aqueous solution was further basified with 10% NaOH solution (pH 10) and extracted with dichloromethane (3×30 ml). The combined organic layers were washed with water (2×20 ml), dried over anhydrous sodium sulfate and the solvent evaporated in vacuo. The oily residue was subjected to vacuum distillation to remove unreacted 4-vinylpyridine (3.9 g). The product was dried under vacuum to remove trace amounts of 4-vinylpyridine to yield 8.7 g (52%) of the title compound 3. 1H-NMR (CDCl3; 400 MHz): 2.90-2.93 (t, 2H, J=6.4 Hz, OCH2CH2), 3.66-3.67 (t, 2H, J=6.8 Hz, OCH2CH2), 5.32 (s, 1H, PhCH(O)Ph), 7.13-7.14 (d, 2H, J=5.6 Hz, 3,5-Pyr-H), 7.17-7.33 (m, 10H, ArH), 8.47-8.48 (d, 2H, J=6.0 Hz, 2,6-Pyr-H).

Workup

  1. temperaturecooled to RT
  2. extractionThe solution was extracted with ethyl acetate (3×30 ml)
  3. customto remove unreacted benzhydrol and side product dibenzhydryl ether
  4. extractionextracted with dichloromethane (3×30 ml)
  5. washThe combined organic layers were washed with water (2×20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent evaporated in vacuo
  8. distillationThe oily residue was subjected to vacuum distillation
  9. customto remove unreacted 4-vinylpyridine (3.9 g)
  10. customThe product was dried under vacuum
  11. customto remove trace amounts of 4-vinylpyridine

Sources & evidence

ORD record
ord-249afde3ce73479bba5631140f465c13
Source dataset
uspto-grants-2012_07
Patent number
US08211916B2

Reaction notes

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