Acetone → Benzenemethanamine, N-(1,1-dimethylethyl)-N-hydroxy-

HRID 359578

Reaction equation

HRID 359578 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)=[O:15]>>[OH:15][N:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 180Acetone2×HCID 76908N-(1,1-Dimethylethyl)benzenemethanamine

Product 1

HCID 10487588Benzenemethanamine, N-(1,1-dimethylethyl)-N-hydroxy-Yield 99.6%

Procedure

A solution of 0.057 M DMD in acetone (47.4 ml, 2.7 mmol) was added to a cold stirred solution of N-tert-butyl-N-benzylamine (Aldrich, 0.4417 g, 2.7 mmol) in acetone (5 ml). The reaction mixture was stirred for fifteen minutes in an ice bath. Solvent was removed on a rotary evaporator to give a white, microcrystalline solid (0.4803 g, 99.6% yield), mp 58-60. Flash chromatography of the solid over silica gel and elution with a 90:10 mixture of petroleum ether (bp 35-60) and ethyl acetate gave the hydroxylamine as a white crystalline solid, mp 60-61.5 (reported mp 71-73, Emmons 1957). Distillation of this material gave a solid with the same mp.

Workup

  1. customSolvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-ee17d6217464416a918d2c66920864ac
Source dataset
uspto-grants-1991_03
Patent number
US05001233

Linked notes

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