N-tert-butylhydroxylamine → HCID 72816255, compound

HRID 2308368Notes

Reaction equation

HRID 2308368 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:12]=1[O:13][CH2:14][O:15][CH3:16])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[C:21]([NH:25][OH:26])([CH3:24])([CH3:23])[CH3:22]>C1C=CC=CC=1>[CH3:16][O:15][CH2:14][O:13][C:12]1[C:11]([C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:10][C:7]([CH:8]=[N+:25]([C:21]([CH3:24])([CH3:23])[CH3:22])[O-:26])=[CH:6][C:5]=1[C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 98586N-tert-butylhydroxylamineHCID 106363293,5-Di-tert-butyl-4-(methoxymethoxy)benzaldehyde

Product 1

HCID 72816255HCID 72816255, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3,5-di-tert-butyl-4-methoxymethoxybenzaldehyde (11.42 g, 40 mmol) in benzene (200 mL) was added tert-butylhydroxylamine (4.0 g, 50 mmol). The resulting solution was refluxed for 72 h until no more aldehyde was detected by TLC (Rf=0.56 for product and 0.78 for starting material in 1:1 hexanes/EtOAc). The solvent was removed in vacuo and the residue was suspended in hexane/EtOAc. The suspension was filtered, washed with hexanes and dried to afford the title compound (69% yield) as a white solid, m.p. 202.2-205.9° C.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationThe suspension was filtered
  3. washwashed with hexanes
  4. customdried

Sources & evidence

ORD record
ord-7bf434021bb24aaf883019639f8e37a9
Source dataset
uspto-grants-2004_12
Patent number
US06835754B2

Reaction notes

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