HCID 23050517, compound → HCID 23050484, compound

HRID 1651819Notes

Reaction equation

HRID 1651819 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]([OH:18])[C:12]#[C:13][C:14]([O:16][CH3:17])=[O:15]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11]([C:12]#[C:13][C:14]([O:16][CH3:17])=[O:15])=[O:18]

Participants

4

Reactant 1

HCID 23050517HCID 23050517, compound

Product 1

HCID 23050484HCID 23050484, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 13.8 g (55 mm ol) of methyl 4-(2,5-dimethoxyphenyl)-4-hydroxy-2-butynoate in 80 ml of methylene chloride is added dropwise at 0° to a suspension of 139 g (1.6 mol) of manganese dioxide in 350 ml of methylene chloride The reaction mixture was stirred at 0° for 1 hour, filtered over magnesium sulphate and concentrated. Crystallization of the residue from methylene chloride/ether yielded methyl 3-(2,5-dimethoxybenzoyl)propiolate of melting point 70°-71°.

Workup

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

Sources & evidence

ORD record
ord-7758478ab7f3460fa392b77dabcd2815
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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