1,4-Dioxane → HCID 20535634, compound

HRID 1156224Notes

Reaction equation

HRID 1156224 reaction equation
I[CH:2]([CH3:24])[CH2:3][O:4][C:5]1[C:10]2[C:11](=[O:20])[CH:12]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:14][C:9]=2[C:8]([CH2:21][CH2:22][CH3:23])=[CH:7][CH:6]=1.[O:25]1CCOCC1>Cl([O-])(=O)(=O)=O.[Ag+]>[OH:25][CH:2]([CH3:24])[CH2:3][O:4][C:5]1[C:10]2[C:11](=[O:20])[CH:12]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:14][C:9]=2[C:8]([CH2:21][CH2:22][CH3:23])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 20535636HCID 20535636, compound

Product 1

HCID 20535634HCID 20535634, compound

Reagents, catalysts & solvents 1

HCID 24562Silver perchlorateCatalyst

Procedure

To a solution of ethyl 5-(2-iodopropoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylate (0.1 g) in 50% aqueous dioxan (15 ml) was added silver perchlorate (0.08 g). The solution was heated at reflux for 4 hours, filtered and evaporated to dryness. The brown, solid residue was crystallised from ethanol giving ethyl 5-(2-hydroxypropoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylate identical in all respects with authentic material.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 4 hours
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe brown, solid residue was crystallised from ethanol

Sources & evidence

ORD record
ord-06e6d7555c274c7184e3b98fcf4f5a92
Source dataset
uspto-grants-1982_06
Patent number
US04335048

Reaction notes

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