Ethyl Acetate → (4-Hydroxyphenyl) 3-pyridyl ketone

HRID 1492513Notes

Reaction equation

HRID 1492513 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15]COC)=[CH:11][CH:10]=2)=[O:8])[CH:2]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:8])[CH:2]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 18950706HCID 18950706, compound

Product 1

HCID 3015820(4-Hydroxyphenyl) 3-pyridyl ketone

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 2.01 g of the thus obtained 4-methoxymethyloxyphenyl 3-pyridyl ketone which has been dissolved in 35 ml of methylene chloride and cooled down to 0° C. was added dropwise 2.01 g of titanium tetrachloride dissolved in 35 ml of methylene chloride. After 2 hours of stirring at room temperature, the resulting reaction mixture was neutralized with saturated sodium hydrogencarbonate solution and mixed with 200 ml of ethyl acetate to separate the organic layer and to extract the water layer with ethyl acetate. Thereafter, the organic phases were combined, washed with saturated sodium chloride aqueous solution and dried using anhydrous magnesium sulfate, followed by the removal of solvents by distillation under a reduced pressure to obtain 1.32 g of 4-hydroxyphenyl 3-pyridyl ketone.

Workup

  1. customthe resulting reaction mixture
  2. customto separate the organic layer
  3. extractionto extract the water layer with ethyl acetate
  4. washwashed with saturated sodium chloride aqueous solution
  5. customdried
  6. customfollowed by the removal of solvents by distillation under a reduced pressure

Sources & evidence

ORD record
ord-dd210a27f2834c52b64c56e51f34b8f2
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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