α,α-DiMethyl-3-(phenylMethoxy)benzeneacetaldehyde synthesis

Yield:70120-09-1 98%

Reaction Conditions:

Stage #1: 2-<3-(benzyloxy)phenyl>-2-methylpropionitrilewith diisobutylaluminium hydride in tetrahydrofuran;hexane at 15 - 20; for 2 h;
Stage #2: with sulfuric acid in tetrahydrofuran;hexane;water at 30; for 2 h;

Steps:

2 Preparation of 2-(3-(benzyloxy)phenyl)-2-methylpropanal (III)

Diisobutylaluminum hydride (300 mL, 0.3 mol of a 1.0 M solution in hexanes) was added dropwise to a cooled (15° C., ice-bath) solution of nitrile II (59.9 g, 0.24 mol) in anhydrous tetrahydrofuran (250 mL). The reaction temperature was maintained at 15-18° C. during the addition. The reaction was then allowed to warm to room temperature and stirred for an additional 2 hours. The reaction was hydrolyzed by addition of a cold solution of conc. H₂SO₄ (35.5 mL) in water (117.5 mL) with the temperature maintained at <30° C. The resultant mixture was stirred for a further 2 hours, then filtered, and the filtrate extracted with diethyl ether (2×250 mL), washed with water (300 mL), brine (300 mL), dried and concentrated under reduced pressure to give crude aldehyde III as a light-yellow oil (59.82 g, 98%) which was used without further purification. M+1=255.

References:

US2006/74086,2006,A1 Location in patent:Page/Page column 26