Thionyl Chloride → HCID 21315732, compound

HRID 236702Notes

Reaction equation

HRID 236702 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[O:21][CH:22]([CH3:24])[CH3:23])=[CH:8][C:7]2=[O:25])([OH:3])=[O:2].S(Cl)(Cl)=O.O1CCO[CH2:32][CH2:31]1>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[O:21][CH:22]([CH3:23])[CH3:24])=[CH:8][C:7]2=[O:25])([O:3][CH2:31][CH3:32])=[O:2]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 312751,4-DioxaneHCID 21315742HCID 21315742, compound

Product 1

HCID 21315732HCID 21315732, compound

Procedure

6-carboxy-2'-isopropoxy-5'-methyl-flavone (4.8 g) in dioxane (30 ml) was treated with thionyl chloride (4 ml) at the reflux temperature for 2 hours. After cooling, the reaction mixture was evaporated to dryness and reacted with an excess of anhydrous ethanol at 50° C. for 1 hour. The mixture was concentrated to a small volume and diluted with water so obtaining, by filtration, 6-carbethoxy-2'-isopropoxy-5'-methyl-flavone (4.7 g).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated to dryness
  3. customreacted with an excess of anhydrous ethanol at 50° C. for 1 hour
  4. concentrationThe mixture was concentrated to a small volume
  5. additiondiluted with water

Sources & evidence

ORD record
ord-f708a8dc283c4ef88fd4c3479eaa447b
Source dataset
uspto-grants-1979_06
Patent number
US04157334

Reaction notes

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