Sulfuric Acid → 2-(3-(Benzyloxy)phenyl)-2-methylpropanal

HRID 2242586Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([C:25]([CH3:29])([CH3:28])[C:26]#N)[CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH:30]S(O)(=O)=O>O1CCCC1.O>[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([C:25]([CH3:29])([CH3:28])[CH:26]=[O:30])[CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 16.5 °C

Procedure

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.

Workup

temperatureto warm to room temperature
temperaturemaintained at <30° C
filtrationfiltered
extractionthe filtrate extracted with diethyl ether (2×250 mL)
washwashed with water (300 mL), brine (300 mL)
customdried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2aa00ad9a7864019aac3f6d015d60daf
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671052B2

Reaction notes

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