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

HRID 26297Notes

Reaction equation

HRID 26297 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]=1)=O)[CH3:2].[C:21]1([CH:28]=CC=[C:24](O)[CH:23]=1)[OH:22].P(Cl)(Cl)(Cl)=O>C1C=CC=CC=1>[OH:22][C:21]1[CH:28]=[C:1]2[C:2]([C:6]([C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=4)[CH:9]=3)=[CH:5][C:4](=[O:20])[O:3]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 24813Phosphorus oxychlorideHCID 3564017HCID 3564017, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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

  1. temperatureto cool
  2. filtrationfiltered
  3. customto give the crude product as a red solid
  4. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-0cc757fde8a24228a1fc98fb32861b81
Source dataset
uspto-grants-1979_04
Patent number
US04148909

Reaction notes

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