Hydrochloric Acid → 4-o-Nitrophenyl-7-hydroxy-coumarin

HRID 26698Notes

Reaction equation

HRID 26698 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[N+:9]([C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[C:14]([CH2:16][C:17](OCC)=[O:18])=O)([O-:11])=[O:10].Cl>CO>[N+:9]([C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[C:14]1[C:8]2[C:1](=[CH:3][C:4]([OH:5])=[CH:6][CH:7]=2)[O:2][C:17](=[O:18])[CH:16]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 10561837Ethyl 2-nitro-beta-oxobenzenepropanoate

Product 1

HCID 544740784-o-Nitrophenyl-7-hydroxy-coumarinYield 63.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.1 mole resorcinol is reacted with 0.1 mole ethyl o-nitrobenzoylacetate in methanol at 0° C. while passing through for one hour gaseous hydrochloric acid, and then maintaining at ambient temperature for 24 hours. After recrystallisation from an acetone-water mixture, there are obtained 18 grams 4-o-nitrophenyl-7-hydroxy-coumarin. This compound melts at 230° C.

Workup

  1. customAfter recrystallisation from an acetone-water mixture, there

Sources & evidence

ORD record
ord-1b7a2826ebc3451ba66fba2d3b5de144
Source dataset
uspto-grants-1979_04
Patent number
US04151291

Reaction notes

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