4-Nitrophenol → HCID 3335330, compound

HRID 2166912Notes

Reaction equation

HRID 2166912 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][C:3]=1[C:19]([OH:21])=[O:20].[CH:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24](O)[CH:23]=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[N+:28]([C:27]1[CH:22]=[CH:23][C:24]([O:20][C:19]([C:3]2[CH:4]=[C:5]([O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]=2[OH:1])=[O:21])=[CH:25][CH:26]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 24386Thionyl ChlorideHCID 4246483HCID 4246483, compound

Product 1

HCID 3335330HCID 3335330, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

335 g (1.15 mol) of 1-hydroxy-4-ethoxycarbonylmethyloxy-2-naphthoic acid and 160 g (1 mol) of p-nitrophenol were added to 1 liter of toluene, and the mixture was stirred while keeping the temperature at 80° C. 130 mols of thionyl chloride were added dropwise over 30 minutes. After stirring for 30 minutes more, the mixture was cooled. The precipitated crystals were filtered off and dried to obtain 271 g (57% yield) of 1-hydroxy-4-ethoxycarbonylmethyloxy-2-naphthoic acid 4-nitrophenyl ester. Melting point: 165°-167° C.

Workup

  1. customat 80° C
  2. stirringAfter stirring for 30 minutes more
  3. temperaturethe mixture was cooled
  4. filtrationThe precipitated crystals were filtered off
  5. customdried

Sources & evidence

ORD record
ord-cf093cc6dfc444569bba6afa115344dd
Source dataset
uspto-grants-1983_06
Patent number
US04390618

Reaction notes

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