Sodium Hydroxide → Boc-4-aminobenzylalcohol

HRID 1854673Notes

Reaction equation

HRID 1854673 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[OH-].[Na+].[C:12](=O)([O:18]C(C)(C)C)[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]>O1CCOCC1.O.C(OCC)C>[C:14]([O:13][C:12]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 693314-Aminobenzyl alcoholHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 10242688Boc-4-aminobenzylalcohol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-aminobenzyl alcohol (2.00 g, 16.2 mmol) in 10 mL of dioxane was added a solution of sodium hydroxide (0.65 g, 16 mmol) in 40 mL of water at room temperature. After addition of di-tert-butyl carbonate (4.95 g, 22.7 mmol), the reaction mixture was stirred at room temperature overnight. The mixture was diluted with diethyl ether, and the solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo to obtain crude 4-(tert-butoxycarbonylamino)benzyl alcohol.

Workup

  1. washthe solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-551149897d714e8097ab56583a6302ce
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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