Hydrochloric Acid → 7-Hydroxy-4-(1-naphthyl)coumarin

HRID 224931

Reaction equation

HRID 224931 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9]1([C:19]([CH2:21][C:22](OCC)=[O:23])=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.Cl>C(O)C>[OH:2][C:1]1[CH:3]=[C:4]2[C:6]([C:19]([C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]=[CH:11][CH:10]=3)=[CH:21][C:22](=[O:23])[O:5]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 2760157Ethyl 3-(naphthalen-8-yl)-3-oxopropanoate

Product 1

HCID 233307447-Hydroxy-4-(1-naphthyl)coumarin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of resorcinol (4.84 g., 0.041 moles) and ethyl 1-naphthoylacetate (10 g., 0.041 moles) in ethanol (50 ml.) was saturated with hydrogen chloride at room temperature (cooling with ice/water) and left to stand in s stoppered flask for 24 hours. The solution was filtered to give the required coumarin as an orange solid (7.8 g., 66%, m.p. 292°-295° C.

Workup

  1. waitleft
  2. customfor 24 hours
  3. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-13d242ac9bd54a34b60200d1f73a5c94
Source dataset
uspto-grants-1980_11
Patent number
US04234726

Linked notes

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