Morpholine → 7-Hydroxyisoflavone

HRID 6278

Reaction equation

HRID 6278 reaction equation
OC1C=C(O)C=CC=1[CH:9]([C:16]([CH:18]([C:25]1[CH:30]=[CH:29]C(O)=CC=1O)C1C=CC=CC=1)=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:33]([O:35][CH:36]([O-])[O-])[CH3:34].N1CC[O:42]CC1>C(Cl)(Cl)Cl>[OH:42][C:29]1[CH:34]=[C:33]2[C:18]([C:16](=[O:17])[C:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:36][O:35]2)=[CH:25][CH:30]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 53630039EthylorthoformateHCID 540149872,4-Dihydroxy-phenyl-benzyl-ketone

Product 1

HCID 53768917-HydroxyisoflavoneYield 90.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 20 g (0.0877 mole) 2,4-dihydroxy-phenyl-benzyl-ketone, 20.7 g (0.14 mole) ethyl-orthoformate and 1 ml of morpholine is stirred on a hot water bath. Crystallization starts after heating for 25 minutes. The inert temperature falls back to 87° C. from 96° C. during the reaction. After stirring for 5 hours the reaction mixture is diluted with 48 ml of chloroform and then one may proceed as disclosed in Example 5. 18.9 g of 7-hydroxy-isoflavone are obtained.

Workup

  1. customCrystallization
  2. temperatureafter heating for 25 minutes
  3. customThe inert temperature falls back to 87° C. from 96° C. during the reaction
  4. stirringAfter stirring for 5 hours the reaction mixture

Sources & evidence

ORD record
ord-90f5082eeee942519d56cfae78d6b65a
Source dataset
uspto-grants-1993_09
Patent number
US05247102

Linked notes

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