2-Amino-4-methylphenol → HCID 4935484, compound

HRID 1821759Notes

Reaction equation

HRID 1821759 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10]([O:14][C:15](=O)[O:16]C(C)(C)C)([CH3:13])([CH3:12])[CH3:11].C(=O)(O)[O-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[C:10]([O:14][C:15](=[O:16])[NH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 72642-Amino-4-methylphenolHCID 516892Sodium BicarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 4935484HCID 4935484, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-amino-4-methyl-phenol (6.15 gm; 50 mmol) in dioxane (100 mL) was added carbonic acid di-tert-butyl ester (9.8 gm; 45 mmol) followed by sodium bicarbonate (12.6 gm; 150 mmol in 75 mL of H2O) After stirring for 8 hours, the reaction was diluted with 100 mL of ethyl acetate and washed with 1N aqueous hydrochloric acid (2×100 mL), saturated aqueous sodium bicarbonate (1×100 mL), and brine (100 mL), then dried (MgSO4), and filtered. The filtered solution was concentrated under reduced pressure to provide the desired (2-Hydroxy-5-methyl-phenyl)-carbamic acid tert-butyl ester as a brown solid (95% yield).

Workup

  1. washwashed with 1N aqueous hydrochloric acid (2×100 mL), saturated aqueous sodium bicarbonate (1×100 mL), and brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtered solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f1ab1c310df041d5ae5e2fdf985fb052
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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