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3-Nitrobenzaldehyde → 2,6-Di-tert-butyl-4-[3-nitro-alpha-(piperidin-1-yl)benzyl]phenol

HRID 52753
Notes
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Reaction equation

HRID 52753 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[C:18]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:23]=1[OH:32])([CH3:21])([CH3:20])[CH3:19]>C1(C)C(C)=CC=CC=1>[C:28]([C:24]1[CH:25]=[C:26]([CH:7]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:27]=[C:22]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:23]=1[OH:32])([CH3:31])([CH3:30])[CH3:29]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 199638702,6-Di-tert-butyl-4-[3-nitro-alpha-(piperidin-1-yl)benzyl]phenolYield 60%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Using the same procedure described in Example 4, 30.2 g (0.2 mol) of 3-nitro-benzaldehyde, 37.4 g (0.44 mol) of piperidine and 39.2 g (0.19 mol) of 2,6-di-tert-butyl-phenol are allowed to react in xylene to give 48.4 g of the title compound as yellow crystals, melting at 157° C.

Sources & evidence

ORD record
ord-df448f9b88ca41edb7f97b5a94ee5ea8
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05616774

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes