Hexane → 4-(4-Nitrophenyl)butanal

HRID 1192881Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13](OC)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].CCCCCC>ClCCl.[H-].C([Al+]CC(C)C)C(C)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH:13]=[O:14])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 21 °C

Procedure

To a stirred solution of methyl 4-(4-nitrophenyl)butanoate (63) (0.45 g, 2.02 mmol) in dichloromethane (30 mL), 1M diisobutylaluminum hydride (DIBAL) solution in hexane (2.62 mL, 2.62 mmol) was added at −78° C. After 30 min, the reaction mixture was quenched with saturated Rochelle's salt solution. The resulting mixture was stirred at 21° C. until both phases were clearly separated and the organic layer was clear. After extraction, the separated organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The crude 4-(4-Nitrophenyl)butanal (64) was purified by flash column chromatography (hexane:ethyl acetate, 8:1) to give 4-(4-Nitrophenyl)butanal (64) (0.28 g, 72%): 1H NMR δ 9.79 (s, 1H), 8.16 (d, 2H, J=8.7 Hz) 7.34 (d, 2H, J=8.7 Hz) 2.77 (t, 2H, J=7.7 Hz) 2.51 (t, 2H, J=7.1 Hz), 1.95-2.04 (m, 2H).

Workup

customthe reaction mixture was quenched with saturated Rochelle's salt solution
customwere clearly separated
extractionAfter extraction
dry with materialthe separated organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe crude 4-(4-Nitrophenyl)butanal (64) was purified by flash column chromatography (hexane:ethyl acetate, 8:1)

Sources & evidence

ORD record: ord-34733428100e409580d57abcdcdbd080
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680291B2

Reaction notes

Loading…