Pyridine → Carbonic Acid (4-nitrophenyl)ester (4-phenoxy-phenyl)ester

HRID 618284Notes

Reaction equation

HRID 618284 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23]>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:22](=[O:23])[O:24][C:25]2[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 132544-PhenoxyphenolHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 54343370Carbonic Acid (4-nitrophenyl)ester (4-phenoxy-phenyl)esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-phenoxyphenol (50 g, 0.27 mol) and pyridine (22 mL, 0.27 mol) in 500 mL of methylene chloride was added under nitrogen dropwise over 1.5 hours to a solution of 4-nitrophenyl chloroformate (54 g, 0.27 mol) in 500 mL of methylene chloride at room temperature. After the addition the reaction was stirred overnight at room temperature. The reaction was extracted two times with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 94.86 g of a light yellow crystalline solid. Recrystallization from methylene chloride-diisopropyl ether gave 69.13 g (73%) of the title compound as a light tan crystalline solid, mp 113-115° C.

Workup

  1. additionAfter the addition the reaction
  2. extractionThe reaction was extracted two times with 1N HCl, multiple times with saturated Na2CO3
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bc39835889014619808914b454a3b5ab
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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