Ethanol → Ipriflavone

HRID 1605174

Reaction equation

HRID 1605174 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 fraction head. Then the major part of solvent is distilled off in 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 fraction head
  2. distillationThen the major part of solvent is distilled off in 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-9195dddb56f746f8a95ceb80bded6348
Source dataset
uspto-grants-1976_04
Patent number
US03949085

Linked notes

Loading…