HCID 53256703, compound → HCID 57467627, compound

HRID 2098940Notes

Reaction equation

HRID 2098940 reaction equation
[CH:1]1([CH:4]([OH:16])[C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=2[OH:15])[C:8]([O:10][CH3:11])=[O:9])[CH2:3][CH2:2]1>[O-2].[Mn+4].[O-2].O1CCOCC1>[CH:1]1([C:4]([C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=2[OH:15])[C:8]([O:10][CH3:11])=[O:9])=[O:16])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 53256703HCID 53256703, compound

Product 1

HCID 57467627HCID 57467627, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a flask with methyl 3-(cyclopropyl(hydroxy)methyl)-4-hydroxybenzoate (T20.2) (845 mg, 0.38 mmol) was added manganese (IV) oxide (1.65 g, 1.9 mmol). Then dioxane 3.5 mL was added and the reaction was heated at reflux for 4 hours. The reaction was filtered and concentrated and silica gel chromatography afforded 693 mg of T20.3 (83%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 hours
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated
  5. customsilica gel chromatography afforded 693 mg of T20.3 (83%)

Sources & evidence

ORD record
ord-e3f8ec9ae4694b2ba638fd09d4921dfe
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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