Benzaldehyde → α-Phenyl-2-pyridineethanol

HRID 443335Notes

Reaction equation

HRID 443335 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C1([Li])C=CC=CC=1.[CH:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CCOCC.C1C=CC=CC=1>[OH:22][CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 79752-MethylpyridineHCID 178506676HCID 178506676, compound

Product 1

HCID 95435α-Phenyl-2-pyridineethanol

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent4×

Conditions

Temperature
0 °C

Procedure

A solution of 4.65 grams (0.05 mole) of 2-picoline in 40 milliliters of ether was added, with stirring, to a solution of phenyllithium (0.05 mole) in 30 milliliters of benzene diluted with 50 milliliters of ether. The solution was refluxed for 1 hour and then cooled to 0° C.; a solution of 5.3 grams (0.05 mole) of benzaldehyde in 30 milliliters of ether was added slowly at 0° C. The reaction mixture was stirred at room temperature for 30 minutes. Water was added, and the organic layer was separated and washed with water. Methylene chloride (100 milliliters) was added; the solution was dried over magnesium sulfate and evaporated under reduced pressure to give a solid. The solid was stirred with 50 milliliters of ether, filtered, and washed with 20 milliliters of ether to give 4.1 grams (40%) of virtually pure product. Recrystallization from 1:1 hexane-acetone gave plates, m.p. 105°-107° C. (Lit. m.p., 110° C., Beyerman, H. C., W. Eveleens, and Y. M. F. Muller, Rec. Trav. Chim., 75, 1956, p. 63).

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. customthe organic layer was separated
  3. washwashed with water
  4. additionMethylene chloride (100 milliliters) was added
  5. dry with materialthe solution was dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give a solid
  8. filtrationfiltered
  9. washwashed with 20 milliliters of ether
  10. customto give 4.1 grams (40%) of virtually pure product
  11. customRecrystallization from 1:1 hexane-acetone
  12. customgave plates, m.p. 105°-107° C. (Lit. m.p., 110° C., Beyerman, H. C., W. Eveleens, and Y. M. F. Muller, Rec. Trav. Chim., 75, 1956, p. 63)

Sources & evidence

ORD record
ord-02d3a4c6c04a40dea94ec1dbf6d2b68e
Source dataset
uspto-grants-1981_04
Patent number
US04259969

Reaction notes

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