Pyridine → 4-Acetoxybiphenyl

HRID 2293008Notes

Reaction equation

HRID 2293008 reaction equation
N1C=CC=CC=1.[C:7](Cl)(=[O:9])[CH3:8].[C:11]1([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[C:7]([O:23][C:20]1[CH:19]=[CH:18][C:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:22][CH:21]=1)(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 71034-Hydroxybiphenyl

Product 1

HCID 3460664-Acetoxybiphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

Pyridine (2 mL) was dissolved in 15 mL of CH2Cl2. The solution was cooled to about 5° C. and stirred while while acetyl chloride (393 mg, 5 mmol) was added slowly. Next, a suspension of p-phenylphenol (0.85 g, 5 mmol) in 20 mL of CH2Cl2 was added dropwise over a 15 min period. The cooling bath was removed and stirring continued for 30 min. The solvents were removed under reduced pressure and 50 mL of ethyl acetate was added to dissolve the solids. The solution was extracted with water, dried over Na2SO4 and evaporated under reduced pressure.

Workup

  1. additionwas added slowly
  2. additionwas added dropwise over a 15 min period
  3. customThe cooling bath was removed
  4. customThe solvents were removed under reduced pressure and 50 mL of ethyl acetate
  5. additionwas added
  6. dissolutionto dissolve the solids
  7. extractionThe solution was extracted with water
  8. dry with materialdried over Na2SO4
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8ccac658627a42aaa8d79c808775bef1
Source dataset
uspto-grants-1997_11
Patent number
US05686258

Reaction notes

Loading…