Acetic Acid → 3-Benzyl-4-fluorobenzaldehyde

HRID 34606Notes

Reaction equation

HRID 34606 reaction equation
[C-:1]#[N:2].[K+].[CH2:4]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(=O)C>O>[CH2:4]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=[O:15])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[C:1]([CH:14]([OH:15])[C:13]1[CH:16]=[CH:17][C:18]([F:19])=[C:11]([CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:12]=1)#[N:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium Cyanide2×HCID 138542803-Benzyl-4-fluorobenzaldehyde

Product 2

HCID 138542803-Benzyl-4-fluorobenzaldehydeHCID 13911474alpha-Cyano-3-benzyl-4-fluorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of potassium cyanide (0.26 g) in water (2 cm3) was added portionwise to a suspension of 3-benzyl-4-fluorobenzaldehyde (0.5 g) in glacial acid (10 cm3) whilst the temperature was maintained at 0° C. After 30 minutes, the reaction mixture was allowed to warm to the ambient temperature (ca. 25° C.), and allowed to stand for a period of 16 hours. A further portion of glacial acetic acid (5 cm3) was added and stirring continued for 8 hours at the ambient temperature. After standing for sixteen hours, a further portion of potassium cyanide (0.26 g) in water (1 cm3) was added, and after the reaction mixture had been allowed to stand for a period of 7 days, it was diluted with water, and extracted with diethyl ether. The ethereal layer was washed sequentially with aqueous sodium bicarbonate, and brine, dried, and the solvent evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel using hexane containing diethyl ether (40% by volume) as eluent to give firstly recovered 3-benzyl-4-fluorobenzaldehyde (0.2 g), and secondly α-cyano-3-benzyl-4-fluorobenzyl alcohol (0.24 g) as a white solid.

Workup

  1. temperatureto warm to the ambient temperature (ca. 25° C.)
  2. waitto stand for a period of 16 hours
  3. waitcontinued for 8 hours at the ambient temperature
  4. waitAfter standing for sixteen hours
  5. waitto stand for a period of 7 days
  6. extractionextracted with diethyl ether
  7. washThe ethereal layer was washed sequentially with aqueous sodium bicarbonate, and brine
  8. customdried
  9. customthe solvent evaporated under reduced pressure
  10. additioncontaining diethyl ether (40% by volume) as eluent

Sources & evidence

ORD record
ord-e6f169fadf73490d8ee2b4aa302af80b
Source dataset
uspto-grants-1988_08
Patent number
US04762835

Reaction notes

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