Ethanol → Ipriflavone

HRID 1862859

Reaction equation

HRID 1862859 reaction equation
O[C:2]1[CH:7]=C(OC(C)C)C=C[C:3]=1[CH:12]([C:19]([CH:21](C1C=CC(OC(C)C)=CC=1O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20])C1C=CC=CC=1.[CH:39]([O-])([O-])[O:40][CH2:41][CH3:42].N1CCOC[CH2:46]1.[CH2:51]([OH:53])[CH3:52]>CN(C)C=O>[CH:51]([O:53][C:7]1[CH:42]=[C:41]2[C:12]([C:19](=[O:20])[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:39][O:40]2)=[CH:3][CH:2]=1)([CH3:46])[CH3:52]

Participants

6

Reactant 4

HCID 702EthanolHCID 8083MorpholineHCID 53630039EthylorthoformateHCID 542779182-Hydroxy-4-isopropyloxy-phenyl-benzyl ketone

Product 1

HCID 3747Ipriflavone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

27 g of 2-hydroxy-4-isopropyloxy-phenyl-benzyl ketone, 22 g of ethyl orthoformate and 5 g of morpholine are boiled for 8 hours in 200 ml of dimethyl formamide. The ethanol formed during the reaction is removed through a fractionation head. Then the major part of solvent is distilled off in a vacuum and the residue is diluted with dilute aqueous hydrochloric acid. The crude product is filtered and recrystallized from acetone, yielding 24 g of 7-isopropyloxy-isoflavone of m.p. 115°-117° C.

Workup

  1. customis removed through a fractionation head
  2. distillationThen the major part of solvent is distilled off in a vacuum
  3. additionthe residue is diluted with dilute aqueous hydrochloric acid
  4. filtrationThe crude product is filtered
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-be2466a5115b41ddafb27a0ee8c57a74
Source dataset
uspto-grants-1979_09
Patent number
US04166862

Linked notes

Loading…