Carbon Dioxide → Methyl 3-iso-pentyloxy-5-nitrobenzoate

HRID 2266941Notes

Reaction equation

[OH-].[Na+].[C:3](=O)=O.[CH2:6]([O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[C:15]([OH:17])=[O:16])[CH2:7][CH:8]([CH3:10])[CH3:9].S(Cl)(Cl)=O>CO>[CH2:6]([O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[C:15]([O:17][CH3:3])=[O:16])[CH2:7][CH:8]([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

In a three-neck reaction flask with a reflux condensor attached to 2 gas wash bottles, the second one filled with NaOH(aq) for absorption of developing CO2 and SO2, 3.7 g (14.6 mmol) 3-iso-pentyloxy-5-nitrobenzoic acid (10) were dissolved in methanol and cooled to 0° C., then 1.6 mL (21.9 mmol) thionyl chloride were added dropwise under stirring. The mixture was refluxed for 4 h, then stirred overnight at r.t.. It was concentrated, then repeatedly taken up in methanol and concentrated again, and put under vacuum. Finally, 2.97 g (76%) of a red-brown liquid, which was found to be sufficiently pure by NMR, were obtained. 1H NMR (CDCl3) δ 8.44 (dd, J1=1.4 Hz, J2=2.2 Hz, 1H), 7.88 (t, J1=2.2 Hz, J2=2.2 Hz, 1H), 7.87 (dd, J1=1.4 Hz, J2=2.2 Hz, 1H), 4.41 (t, J=6.8 Hz, 2H, PhOCH2CH2CH(CH3)2), 3.94 (s, 3H, OCH3), 1.88-1.65 (m, 3H), 0.99 (d, J=6.6 Hz, 6H, CH(CH3)2).

Workup

customIn a three-neck reaction flask with a reflux condensor attached to 2 gas
washwash bottles
temperatureThe mixture was refluxed for 4 h
stirringstirred overnight at r.t.
concentrationIt was concentrated
concentrationconcentrated again
customwere obtained

Sources & evidence

ORD record: ord-417ba3e960704f95a1837f721e8e608c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858737B2

Reaction notes

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