Nitric Acid → 2-Naphthalenecarboxylic acid, 1-hydroxy-4-nitro-, phenyl ester

HRID 2350842Notes

Reaction equation

HRID 2350842 reaction equation
[N+:1]([O-:4])(O)=[O:2].[O:5]([C:12]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]=1[OH:24])=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)(Cl)Cl>[N+:1]([C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([OH:24])=[C:14]([C:12]([O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:13])[CH:23]=1)([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 67236Phenyl 1-hydroxy-2-naphthoate

Product 1

HCID 1033292-Naphthalenecarboxylic acid, 1-hydroxy-4-nitro-, phenyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

12 ml of fuming nitric acid (d=1.5) was added dropwise to a solution of 53 g of 2-phenoxycarbonyl-1-naphthol dissolved in 200 ml of chloroform was added dropwise 12 cc of fuming nitric acid (d=1.5) at 10° C. to 30° C. After 30 minutes, the precipitated crystals were filtered, washed well with cooled chloroform to obtain the desired product at a yield of 62%. The product had m.p. of 157° C., and was confirmed by NMR, Mass spectra.

Workup

  1. filtrationthe precipitated crystals were filtered
  2. washwashed well with cooled chloroform

Sources & evidence

ORD record
ord-ab1b48f1ee9b47608c0788d370089e11
Source dataset
uspto-grants-1989_10
Patent number
US04871655

Reaction notes

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