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

HRID 1468519Notes

Reaction equation

HRID 1468519 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-20aeade816f344a594c7d8723cd72c4a
Source dataset
uspto-grants-2015_04
Patent number
US09000173B2

Reaction notes

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