Maltol → HCID 86741482, compound

HRID 330063Notes

Reaction equation

HRID 330063 reaction equation
[CH3:1][C:2]1[O:8][CH:7]=[CH:6][C:4](=[O:5])[C:3]=1[OH:9].[Cl-].[Zn+2:11].[Cl-].[Zn].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(Cl)(Cl)Cl>[Zn:11].[CH3:1][C:2]1[O:8][CH:7]=[CH:6][C:4](=[O:5])[C:3]=1[OH:9]

Participants

7

Reactant 4

HCID 8369Maltol3×HCID 10340Sodium CarbonateHCID 23994ZincHCID 3007855Zincchloride

Product 1

HCID 86741482HCID 86741482, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A chloroform solution of maltol (1) is mixed with a 1M solution of zinc chloride in ethanol to provide a 2:1 molar ratio of maltol: zinc in the mixture. After 5 minutes at 20° C., a 10 molar excess of solid sodium carbonate is added and the mixture is stirred for 10 minutes. The mixture is then filtered and the solvent evaporated to give the neutral complex containing maltol and Zn++ in a 2:1 proportion. Recrystallisation of the 2:1 complex from ethanol gives a white crystalline solid in essentially quantitative yield, m.p. 203°-204° C. (with decomposition); νmax (nujol) 1632, 1603 cm-1 ; δ(d6DMSO) 7.96 (d, 1H), 6.40 (d, 1H), 2.20 (s, 3H).

Workup

  1. customto provide a 2
  2. filtrationThe mixture is then filtered
  3. customthe solvent evaporated
  4. customto give the neutral complex
  5. customRecrystallisation of the 2:1 complex from ethanol
  6. customgives a white crystalline solid in essentially quantitative yield, m.p. 203°-204° C. (with decomposition)

Sources & evidence

ORD record
ord-f40fb2c0959745908741e70b9d726eab
Source dataset
uspto-grants-1990_01
Patent number
US04894455

Reaction notes

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