Phloroglucinol → Flamenol

HRID 2296390

Reaction equation

HRID 2296390 reaction equation
[CH3:1][O:2][C:3]1[C:13]2C=C[O:16][C:12]=2[CH:11]=[C:10]2[C:4]=1C=CC([O:9]2)=O.C1(C=C(O)C=C(O)C=1)O>>[CH3:1][O:2][C:3]1[CH:13]=[C:12]([OH:16])[CH:11]=[C:10]([OH:9])[CH:4]=1

Participants

3

Reactant 2

HCID 359Phloroglucinol2×HCID 2355Bergapten

Product 1

HCID 71648Flamenol

Procedure

The present invention also relates to a new synthesis of 5-methoxy-psoralen of the formula: ##STR3## starting from phloroglucinol of the formula: ##STR4## In this synthesis the phloroglucinol is methylated to obtain phloroglucinol mono-methyl ether, which is in turn cyclicized to obtain 6-hydroxy-4-methoxy-3-coumaranone; the coumaranone is reduced in one step to obtain 6-hydroxy-4-methoxy coumaran; the coumaran is then cyclicized to obtain 3,4,4',5'-tetrahydro-5 methoxy psoralen; and that product is hydrogenated to yield 5-methoxy-psoralen.

Sources & evidence

ORD record
ord-f61e694bdfc946b4bc8af343b3e6f379
Source dataset
uspto-grants-1984_01
Patent number
US04429138

Linked notes

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