4-Aminophenol → Benzyl (4-hydroxyphenyl)carbamate

HRID 2095750Notes

Reaction equation

HRID 2095750 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.C(=O)([O-])O.[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>O1CCCC1>[OH:8][C:3]1[CH:4]=[CH:5][C:6]([NH:7][C:15](=[O:16])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 293061Benzyl (4-hydroxyphenyl)carbamateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of p-aminophenol (7.0 g, 63.9 mmol) in tetrahydrofuran (105 mL) was added saturated aqueous sodium hydrogen carbonate (70 mL), and benzyl chloroformate (12.0 g, 70.3 mmol) was added dropwise at 0° C. After stirring at room temperature for 16 hr, the reaction mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated brine (100 mL) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was washed with hexane/ethyl acetate (=4/1) and collected by filtration to give the title compound (8.2 g, 53%).

Workup

  1. additionwas added dropwise at 0° C
  2. extractionthe reaction mixture was extracted with ethyl acetate (200 mL)
  3. washThe organic layer was washed with saturated brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washThe residue was washed with hexane/ethyl acetate (=4/1)
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-67e8d01ae8044287a74b5e25d51e319b
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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