HCID 86743958, compound → HCID 86743959, compound

HRID 1651366Notes

Reaction equation

HRID 1651366 reaction equation
[OH:1][CH:2](/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11](/[CH:10]=[CH:9]/[C:2](=[O:1])[C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6])=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 86743958HCID 86743958, compound

Product 1

HCID 86743959HCID 86743959, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.7 g (43.4 mmol) of methyl (E)-4-hydroxy-6-(4-methoxyphenyl)-5-hexen-2-ynoate in 150 ml of methylene chloride was added dropwise at 0° to a suspension of 56.7 g (652 mmol) of manganese dioxide in 200 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 yielded methyl (E)-6-(4-methoxyphenyl)-4-oxo-5-hexen-2-ynoate of melting point 70°.

Workup

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

Sources & evidence

ORD record
ord-9d36af4c7c994e98b8333887d7e72e28
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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