HCID 23050515, compound → HCID 18991491, compound

HRID 1651813Notes

Reaction equation

HRID 1651813 reaction equation
[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:15][C:12]1[CH:11]=[CH:10][C:9]([C:2]([C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6])=[O:1])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 23050515HCID 23050515, compound

Product 1

HCID 18991491HCID 18991491, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8.1 g (39.7 mmol) of methyl 4-hydroxy-4-(4-methylphenyl)-2-butynoate in 100 ml of methylene chloride was added dropwise at 0° to a suspension of 97 g (1.1 mol) of manganese dioxide in 200 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-(4-methylbenzoyl)propiolate of melting point 55°-56°.

Workup

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

Sources & evidence

ORD record
ord-41aee4932cee44739c278c9c75312f71
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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