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

HRID 1679138Notes

Reaction equation

CCCC(O[C:7]([C:9]1[CH:14]=[CH:13][C:12]2[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:11]=2[CH:10]=1)=O)=O.[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=CC=1>>[OH:22][C:21]1[CH:23]=[C:24]2[C:26]([C:7]([C:9]3[CH:14]=[CH:13][C:12]4[C:11](=[CH:18][CH:17]=[C:16]([O:19][CH3:20])[CH:15]=4)[CH:10]=3)=[CH:39][C:34](=[O:30])[O:25]2)=[CH:27][CH:28]=1

Participants

Reactant 4

HCID 241Benzene

HCID 5054Resorcinol

HCID 24813Phosphorus oxychloride

HCID 54028537HCID 54028537, 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. Recrystallization 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
customRecrystallization from ethanol

Sources & evidence

ORD record: ord-0b3b8d42bc25470ebcb4d97f8fddad1b
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04079066

Reaction notes

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