Acetic Acid → 2-{p-[(3,5-Dichloro-2-pyridyl)oxy]phenoxy}propionaldehyde

HRID 249198Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:9][C:10]2[CH:23]=[CH:22][C:13]([O:14][CH:15]([CH3:21])[C:16](OCC)=[O:17])=[CH:12][CH:11]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)C.CCCCCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:9][C:10]2[CH:23]=[CH:22][C:13]([O:14][CH:15]([CH3:21])[CH:16]=[O:17])=[CH:12][CH:11]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: -55 °C

Procedure

A solution of ethyl 2-{p-[(3,5-dichloro-2-pyridyl)oxy]phenoxy]propionate (1,455 g, 4.06 mol) in toluene (12 L) is cooled to -55° C. under a nitrogen atmosphere and diisobutylaluminum hydride (5.42 L of a 1.0M solution) is added over 2 hours. The reaction mixture is then stirred for 5 hours at -55° C. and glacial acetic acid (1.8 L) is added dropwise, while allowing the mixture to exotherm to 15° C. Heptane 2 L) is added and the mixture is washed sequentially with 5% hydrochloric acid solution, water, saturated sodium bicarbonate solution and water and concentrated in vacuo to obtain the title product as a yellow-orange liquid (1,159 g) which is identified by 1H NMR spectral analysis.

Workup

customto exotherm to 15° C
washthe mixture is washed sequentially with 5% hydrochloric acid solution, water, saturated sodium bicarbonate solution and water
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ed7afa8dff094a31816d1b7700d1a6e0
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05213606

Reaction notes

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