O-Methylhydroxylamine hydrochloride → 3-(3,4-Dichlorophenyl)-propionaldehyde o-methyloxime

HRID 1836541Notes

Reaction equation

HRID 1836541 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[O:14]([NH2:16])[CH3:15]>>[CH3:15][O:14][N:16]=[CH:11][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

3

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 234995723-(3,4-Dichlorophenyl)propanal

Product 1

HCID 740573273-(3,4-Dichlorophenyl)-propionaldehyde o-methyloximeYield 91%

Procedure

Reaction of 3-(3,4-dichlorophenyl)-propionaldehyde (Heck, J. Amer. Chem. Soc., 90, 1968, 5526) with methoxylamine hydrochloride as described in the preparation of compound 3-A gave the title oxime ether as a clear oil (91% yield), bp 80-90° C./0.5 torr (bulb to bulb distillation, air bath temperature). 1HNMR indicated a 55:45 mixture of E- and Z-isomers. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.63 and 2.76 (2H, 2 m, CH2), 2.9 (2H, m, CH2), 3.96 and 4.01 (3H, 2 s, OCH3), 6.77 (t, J=5.5 Hz, CH), 7.16-7.5 (3H, m, aromatics and CH).

Workup

  1. customgave

Sources & evidence

ORD record
ord-82b9d1c85ff949659a5b29ca4f5b0088
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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