HCID 23050497, compound → HCID 23050503, compound

HRID 1651846Notes

Reaction equation

HRID 1651846 reaction equation
[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)[C:3]#[C:4][CH2:5][O:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:10][C:9]([CH3:11])=[CH:8][CH2:7][O:6][CH2:5][C:4]#[C:3][C:2]([C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)=[O:1]

Participants

4

Reactant 1

HCID 23050497HCID 23050497, compound

Product 1

HCID 23050503HCID 23050503, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 34.2 g (125 mmol) of 1-hydroxy-4-[(3-methyl-2-butenyl)oxy)-1-(3,4-(methylenedioxy)phenyl]-2-butyne in 350 ml of methylene chloride was added dropwise at 0° to a suspension of 163 g (1.87 mol) of manganese dioxide in 500 ml of methylene chloride. The reaction mixture was stirred at 0° for 2 hours, filtered over magnesium sulphate and concentrated. The crude product was recrystallized from ether/hexane at -50°. There was obtained 4-[(3-methyl-2-butenyl)oxy]-1-[3,4-(methylenedioxy)phenyl]-2-butyn-1-one as pale yellow crystals which melt at room temperature.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated
  3. customThe crude product was recrystallized from ether/hexane at -50°

Sources & evidence

ORD record
ord-1ceb8e6c92484d6cb99ea6798632f8fb
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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