Benzyl chloroformate → benzyl N-(4-hydroxy-3-methylphenyl)carbamate

HRID 1993589Notes

Reaction equation

HRID 1993589 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOC(C)=O>[CH2:10]([O:17][C:18](=[O:19])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 760815-Amino-2-hydroxytoluene

Product 1

HCID 68538458benzyl N-(4-hydroxy-3-methylphenyl)carbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Amino-2-methyl-phenol (717 mg, 5.8 mmol) and benzyloxycarbonyl chloride (1.09 g, 6.4 mmol) are stirred in a suspension of AcOEt/concentrated Na2CO3 solution (50 mL/50 mL) for 7 h. The organic phase is concentrated under reduced pressure and flash chromatographed (silica gel, 3.8×66 cm, AcOEt/hexane=1:3): M+H=257.9; HPLC (System 1): 5.43 min.

Workup

  1. concentrationThe organic phase is concentrated under reduced pressure and flash
  2. customchromatographed (silica gel, 3.8×66 cm, AcOEt/hexane=1:3)
  3. custom5.43 min.

Sources & evidence

ORD record
ord-0fc3d4811abf4273b435294bb40ebae4
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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