Maltol → HCID 86741482, compound

HRID 978344Notes

Reaction equation

HRID 978344 reaction equation
[Cl-].[Zn+2:2].[Cl-].[CH3:4][C:5]1[O:11][CH:10]=[CH:9][C:7](=[O:8])[C:6]=1[OH:12].[Zn].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(Cl)(Cl)Cl>[Zn:2].[CH3:4][C:5]1[O:11][CH:10]=[CH:9][C:7](=[O:8])[C:6]=1[OH:12]

Participants

7

Reactant 4

HCID 8369Maltol2×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-1b4acf71389941a7b87d9ad6069de81f
Source dataset
uspto-grants-1987_05
Patent number
US04665064

Reaction notes

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