2-(Propan-2-yloxy)benzaldehyde → 2-Isopropoxy-benzaldehyde o-methyloxime

HRID 2181118Notes

Reaction equation

HRID 2181118 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O)([CH3:3])[CH3:2].Cl.[O:14]([NH2:16])[CH3:15]>>[CH3:15][O:14][N:16]=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 2500782-(Propan-2-yloxy)benzaldehydeHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 730945022-Isopropoxy-benzaldehyde o-methyloxime

Procedure

Reaction of 2-isopropoxybenzaldehyde (Hach, Collect. Czech. Commun., 23, 1958, 1902-1907) with methoxylamine hydrochloride as described in the preparation of compound 1-A gave the title oxime ether as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8:2) (96% yield). 1HNMR indicated a 95:5 mixture of E- and Z-isomers. 1HNMR 400 MHz (CDCl3) δ (ppm): (E-isomer) 1.33 (6H, d, J=6.1 Hz, CH3), 3.97 (3H, s, OCH3), 4.56 (1H, m, CH), 6.90 (2H, m, aromatics), 7.30 (1H, m, aromatic), 7.79 (1H, dd, J=2.0 Hz and J=7.6 Hz, aromatic), 8.47 (1H, s, CH).

Sources & evidence

ORD record
ord-3cd8adf9379942668c8fd45e4ed3e63c
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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