Acetic Acid → HCID 14985924, compound

HRID 1654807Notes

Reaction equation

HRID 1654807 reaction equation
[C-]#N.[Na+].[CH:4]([C:6]1[C:7]([OH:20])=[CH:8][C:9]2[O:14][C:13]([CH3:15])=[CH:12][C:11](=[O:16])[C:10]=2[C:17]=1[O:18][CH3:19])=[O:5].[C:21](O)(=[O:23])C>CO.C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[OH:20][C:7]1[C:6]([C:4]([O:23][CH3:21])=[O:5])=[C:17]([O:18][CH3:19])[C:10]2[C:11](=[O:16])[CH:12]=[C:13]([CH3:15])[O:14][C:9]=2[CH:8]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 817924H-1-Benzopyran-6-carboxaldehyde, 7-hydroxy-5-methoxy-2-methyl-4-oxo-

Product 1

HCID 14985924HCID 14985924, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.6 g (53 mmol) of sodium cyanide and then 18.50 g (223 mmol, 25 eq.) of activated manganese dioxide are added to 2 g (8.5 mmol) of 6-formyl-7-hydroxy-5-methoxy-2-methyl-4H -benzopyran-4-one (A. SCHONBERG, N. BADRAN and N. A. STARKONSKY, J. Am. Chem. Soc., 1953, 75, 4992) suspended in 105 ml of methanol acidified with 2.6 ml of acetic acid. After having been stirred for 4 hours at room temperature, the reaction mixture, diluted with 200 ml of ethyl acetate, is filtered to remove insoluble material (excess MnO2) and the solvents are evaporated. The powdery residue is taken up in water and filtered. 1.80 g of a beige powder are obtained.

Workup

  1. filtrationis filtered
  2. customto remove insoluble material (excess MnO2)
  3. customthe solvents are evaporated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-21a3ecab3e8e4eb2b075bde5701355d3
Source dataset
uspto-grants-1995_04
Patent number
US05409952

Reaction notes

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