HCID 23050473, compound → HCID 23050519, compound

HRID 1651816Notes

Reaction equation

HRID 1651816 reaction equation
[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[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]>[CH3:16][S: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 23050473HCID 23050473, compound

Product 1

HCID 23050519HCID 23050519, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 11.6 g (49 mmol) of methyl 4-hydroxy-4-[4-(methylthio)phenyl]-2-butynoate in 300 ml of methylene chloride was added dropwise at 0° to a suspension of 124 g (1.42 mol) of manganese dioxide in 300 ml of methylene chloride. The reaction mixture was stirred at 0° for 2 hours filtered over magnesium sulphate and concentrated. Crystallization of the residue from ether/hexane yielded methyl 3-[4-(methylthio)benzoyl]propiolate of melting point 74°-76°.

Workup

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

Sources & evidence

ORD record
ord-b72d4a76e97e40d9b8e38f74eb903733
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

Loading…