Sodium Bicarbonate → (4-Amino-2,5-dimethylphenyl)methanol

HRID 1055327Notes

Reaction equation

HRID 1055327 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]2OCC[O:17]2)=[CH:11][C:10]=1[CH3:21])C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CCO.CCOC(C)=O.[Pd]>[NH2:8][C:9]1[C:10]([CH3:21])=[CH:11][C:12]([CH2:16][OH:17])=[C:13]([CH3:15])[CH:14]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 57461075Dibenzyl-(4-[1,3]dioxolan-2-yl-2,5-dimethyl-phenyl)amine

Product 1

HCID 66770156(4-Amino-2,5-dimethylphenyl)methanol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of dibenzyl-[4-(1,3-dioxolan-2-yl)-2,5-dimethylphenyl)amine (2.00 g, 5.35 mmol) in EtOH (14.0 mL) and EtOAc (7.00 mL) was flushed with nitrogen for 3 min and then sodium bicarbonate (0.200 g, 2.38 mmol) and palladium on activated carbon (10 wt. %, ˜50% water; 0.800 g, 0.360 mmol) were added. The reaction mixture was flushed with hydrogen gas for 3 min and then stirred under a hydrogen atmosphere (balloon) for 3 h. The mixture was then filtered through a pad of Celite and the pad washed with MeOH (10 mL). The filtrate was concentrated under reduced pressure to give the title compound, which was used without any further purification.

Workup

  1. customThe reaction mixture was flushed with hydrogen gas for 3 min
  2. filtrationThe mixture was then filtered through a pad of Celite
  3. washthe pad washed with MeOH (10 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e31e3959454343a8bed71f02f96490f2
Source dataset
uspto-grants-2016_07
Patent number
US09394275B2

Reaction notes

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