Acetic Acid → 2-[p-(Benzyloxy)phenoxy]propionaldehyde

HRID 249202Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([O:18][C:19]1[CH:31]=[CH:30][C:22]([O:23][CH:24]([CH3:29])[C:25](OC)=[O:26])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([O:23][CH:24]([CH3:29])[CH:25]=[O:26])=[CH:30][CH:31]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -65 °C

Procedure

A 1.5 molar solution of diisobutylaluminum hydride in toluene (138 mL, 0.207 mol) is added dropwise to a mixture of methyl 2-[p-(benzyloxy)phenoxy]propionate (56.4 g, 0.197 mol) in toluene at -65° C. under a nitrogen atmosphere. The reaction mixture is stirred at -65° C. for 5 hours. Acetic acid (70 mL) is added dropwise and the reaction mixture is warmed to room temperature, diluted with hexanes, washed with 10% hydrochloric acid solution and water, dried and concentrated in vacuo to obtain an oil. Flash chromatography of the oil using silica gel and eluting with a 1:1 methylene chloride/hexanes solution gives the title product as a white solid (21.44 g, mp 50°-51° C.).

Workup

temperaturethe reaction mixture is warmed to room temperature
washwashed with 10% hydrochloric acid solution and water
customdried
concentrationconcentrated in vacuo
customto obtain an oil
washeluting with a 1:1 methylene chloride/hexanes solution

Sources & evidence

ORD record: ord-266f2494cc3d429e89e468a3432dc9cb
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05213606

Reaction notes

Loading…