Acetate → HCID 14427484, compound

HRID 2296391Notes

Reaction equation

HRID 2296391 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:8]([OH:9])[CH:7]=[C:5]([OH:6])[CH:4]=1.Cl[CH2:12]C#N.Cl.[C:16]([O-])(=[O:18])C>[Cl-].[Zn+2].[Cl-]>[OH:9][C:8]1[CH:10]=[C:3]2[C:4]([C:16](=[O:18])[CH2:1][O:2]2)=[C:5]([O:6][CH3:12])[CH:7]=1

Participants

6

Reactant 4

HCID 175AcetateHCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 71648Flamenol

Product 1

HCID 14427484HCID 14427484, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A process of synthesizing 5-methoxy psoralene comprising methylating phloroglucinol with methanol to obtain the monomethyl ether of phloroglucinol; cyclizing the phloroglucinol monomethyl ether by first reacting with chloracetonitrile in the presence of gaseous HCl and zinc chloride then heating with postassium acetate to obtain 6-hydroxy-4-methoxy-3-coumaranone; reducing the 6-hydroxy-4-methoxy-3-courmaranone by direct reduction in the presence of a hydrazine hydrate catalyst to obtain 6-hydroxy-4-methoxy coumaran; cylizing the 6-hydroxy-4-methoxy-coumaran by reacting with acrylonitrile in the presence of HCl and zinc chloride to obtain 3,4,4',5'-tetra-hydro-5-methoxy psoralene and dehydrogenerating the 3,4,4',5' tetrahydro-5-methoxy psoralen to obtain 5-methoxy psoralene.

Sources & evidence

ORD record
ord-c51ffe28f47e41dcb31aa04326977c9f
Source dataset
uspto-grants-1984_01
Patent number
US04429138

Reaction notes

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