Benzene → 7-Hydroxy-4-(6-methoxynaphthalen-2-yl)-2H-1-benzopyran-2-one

HRID 262146Notes

Reaction equation

C(OC([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[C:8]=1CC)=O)(=O)C.[C:21]1([CH:28]=[CH:27][CH:26]=[C:24]([OH:25])[CH:23]=1)[OH:22].P(Cl)(Cl)(Cl)=[O:30].[CH:34]1[CH:39]=CC=C[CH:35]=1>>[OH:22][C:21]1[CH:23]=[C:24]2[C:26]([C:35]([C:7]3[CH:8]=[CH:9][C:10]4[C:15](=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[CH:11]=4)[CH:16]=3)=[CH:34][C:39](=[O:30])[O:25]2)=[CH:27][CH:28]=1

Participants

Reactant 4

HCID 241Benzene

HCID 5054Resorcinol

HCID 24813Phosphorus oxychloride

HCID 54093168HCID 54093168, compound

Product 1

HCID 205704997-Hydroxy-4-(6-methoxynaphthalen-2-yl)-2H-1-benzopyran-2-oneYield 69%

Procedure

A stirred solution of ethyl(6-methoxy-2-naphthoyl) acetate (36 g, 0.132 mole), resorcinol (14.6 g, 0.132 mole) and phosphoryl chloride (32 ml) in benzene (200 ml) was refluxed for 3 hours. The reaction mixture was allowed to cool, poured into ice/water and filtered to give the crude product as a red solid. Recrystallisation from ethanol gave 7-hydroxy-4(6-methoxy-2-naphthyl)coumarin (28.9 g, 69%) m.p. 223°-225° C.

Workup

temperatureto cool
filtrationfiltered
customto give the crude product as a red solid
customRecrystallisation from ethanol

Sources & evidence

ORD record: ord-8c8faba982dc45c6b385709733ff4986
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04153617

Reaction notes

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