4-Nitrophenol → HCID 178476832, compound

HRID 542700Notes

Reaction equation

HRID 542700 reaction equation
NC1C=CC(C[P:7](=O)([O:11]CC)[O:8][CH2:9][CH3:10])=CC=1.ClC(OCC1C=CC=CC=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.[CH:40]1[C:45]([N+:46]([O-:48])=[O:47])=[CH:44][CH:43]=[C:42]([OH:49])[CH:41]=1>C(=O)(O)[O-].[Na+].C(Cl)(Cl)Cl>[PH:7](=[O:11])([O:49][C:42]1[CH:43]=[CH:44][C:45]([N+:46]([O-:48])=[O:47])=[CH:40][CH:41]=1)[O:8][CH2:9][CH3:10]

Participants

8

Reactant 5

HCID 9804-NitrophenolHCID 1049PyridineHCID 10387Benzyl chloroformateHCID 24819Phosphorus pentachlorideHCID 88358Diethyl p-aminobenzylphosphonate

Product 1

HCID 178476832HCID 178476832, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Diethyl p-aminobenzylphosphonate (1) (Aldrich Chemical Co., Milwaukee, WI) was converted to the p-carbobenzyloxy derivative (2) by the addition of 1.2 equivalents benzyl chloroformate in saturated aqueous sodium bicarbonate (NaHCO3) for 20 minutes at 23° C. That derivative was treated with 1.1 equivalents phosphorous pentachloride (PCl5) in chloroform at 50° C. for 2 hours. Pyridine (5 equivalents) and p-nitrophenol (3 equivalents) were added at 23° C. and subsequent workup provided the ethyl p-nitrophenyl phosphonate (3).

Sources & evidence

ORD record
ord-557e42d8b708457abe6792d4987dd115
Source dataset
uspto-grants-1987_04
Patent number
US04659567

Reaction notes

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