N-[(4-tert-butylphenyl)methylidene]hydroxylamine → [4-(4-tert-Butyl-benzylideneaminooxymethyl)-phenyl]-acetic Acid
Reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH:9]=[N:10][OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:9]=[N:10][O:11][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:20][CH:21]=2)=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]Participants
3
Procedure
The title compound was prepared as a white solid (0.193 g, 41%) from 4-tert-butyl-benzaldehyde oxime and 4-bromomethyl-phenyl-acetic acid using a procedure similar to example 2. mp=93.3-96.2° C.; mass spectrum (−APCI, M−H) m/z 324. 1H NMR (400 MHz, DMSO-d6); δ 12.30 (bs, 1H), 8.23 (s, 1H), 7.52 (d, 2H), 7.42 (d, 2H), 7.33 (d, 2H), 7.24 (d, 2H), 5.10 (s, 2H), 3.55 (s, 2H), 1.25 (s, 9h). Elemental analysis: Calcd. for C20H23NO3: C, 73.82; H, 7.12; N, 4.30, Found: C, 73.15; H, 7.14; N, 4.01.
Sources & evidence
- ORD record
- ord-65230aef10034faebeebfeedd7ed77b1
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420083B2
Reaction notes
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