2-Amino-5-methylphenol → 328267-64-7

HRID 2092402Notes

Reaction equation

HRID 2092402 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].[C:10](=O)([O:16]C(C)(C)C)[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[C:12]([O:11][C:10](=[O:16])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[CH:6][C:7]=1[OH:8])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 760822-Amino-5-methylphenolHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 53495421328267-64-7Yield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-amino-m-cresol (5 g, 40.6 mmol) in DCM (100 mL) was added di-tert-butyl carbonate (9.4 ml, 40.6 mmol), under an argon atmosphere. The resulting mixture was stirred for 18 h at RT, quenched by addition of a saturated aqueous solution of NaHCO3 and extracted with DCM. The organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated to afford 9.1 g of the title compound as a black oil which was used as a crude material. HPLC: LtRet=4.86 min; LC-MS: m/z 224.3 [M+H]+.

Workup

  1. customquenched by addition of a saturated aqueous solution of NaHCO3
  2. extractionextracted with DCM
  3. washThe organic phase was washed with a saturated aqueous solution of NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bede0cc802a40618082152cfdae8409
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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