Methyl 4-Formylbenzoate → 4-Carbomethoxybenzaldehyde o-methyloxime

HRID 1836495Notes

Reaction equation

HRID 1836495 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.Cl.[O:14]([NH2:16])[CH3:15]>>[CH3:15][O:14][N:16]=[CH:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 6063154-Carbomethoxybenzaldehyde o-methyloximeYield 96%

Procedure

Reaction of methyl 4-formylbenzoate with methoxylamine hydrochloride as described in the preparation of compound 3-A gave the title oxime ether (96% yield) as a white solid (mixture of E- and Z-isomers). The E-isomer was obtained as white crystals from hexane; mp 66-67° C. (Lit. mp 65-66° C., Cooks, R. G.; Varvoglis, A. G. Org. Mass Spectrum., 5, 1971, 687). 1HNMR 400 MHz (DMSO-d6) δ (ppm): (E-isomer) 3.86 (3H, s, OCH3), 3.93 (3H, s, OCH3), 7.75 (2H, d, aromatics), 7.98 (2H, d, aromatics), 8.32 (1H, s, CH).

Workup

  1. customgave

Sources & evidence

ORD record
ord-74ebd26448bb4fafb35a9475b897b731
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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