HCID 23050471, compound → HCID 23050509, compound

HRID 1651804Notes

Reaction equation

HRID 1651804 reaction equation
[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:16][O:17][C:11]=2[CH:10]=1)[C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:16]1[O:15][C:12]2[CH:13]=[CH:14][C:9]([C:2]([C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6])=[O:1])=[CH:10][C:11]=2[O:17]1

Participants

4

Reactant 1

HCID 23050471HCID 23050471, compound

Product 1

HCID 23050509HCID 23050509, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution cf 7.3 g (31 mmol) of methyl 4-hydroxy-4[3,4-(methylenedioxy)phenyl]-2-butynoate in 80 ml of methylene chloride was added dropwise at 0° to a suspension of 77 g (0.89 mol) of manganese dioxide in 150 ml of methylene chloride. The reaction mixture was stirred at 0° for 30 minutes, filtered over magnesium sulphate and concentrated. Crystallization of the residue from ether/hexane yielded methyl 3-[3,4-(methylenedioxy) benzoyl)-propiolate of melting point 95°-97°.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated
  3. customCrystallization of the residue from ether/hexane

Sources & evidence

ORD record
ord-a42d59f12776408384fea68da711ad8c
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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