Ammonium formate → 4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenol

HRID 1619436Notes

Reaction equation

HRID 1619436 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17][CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:21][C:18]1([CH3:22])[O:17][CH2:16][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:20][O:19]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 675165485-(4-(Benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxane

Product 1

HCID 675102564-(2,2-Dimethyl-1,3-dioxan-5-yl)phenolYield 37.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
30 °C

Procedure

To a suspension of 10% Pd/C (85 mg) in methanol was added a solution of 5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxane (850.0 gm, 0.00775 moles) in methanol (20 ml). To this was added ammonium formate (900 mg, 0.0143 mole) and the reaction mixture was refluxed for 2 hrs. The reaction mixture was then cooled to 30° C. and filtered through celite. The filtrate was evaporated under reduced pressure and residue was dissolved in dichloromethane and filtered through celite. The filtrate was evaporated under reduced pressure to yield 600 mg product as white solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hrs
  2. filtrationfiltered through celite
  3. customThe filtrate was evaporated under reduced pressure and residue
  4. dissolutionwas dissolved in dichloromethane
  5. filtrationfiltered through celite
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9500a318845c4d4cbbe72f00facda76d
Source dataset
uspto-grants-2014_07
Patent number
US08772302B2

Reaction notes

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