Methanol → Methyl 3-(4-nitrophenyl)-2-propenoate

HRID 386435

Reaction equation

HRID 386435 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].OS(O)(=O)=O.[CH3:20]O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:20])=[O:11])=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 701562-Propenoic acid, 3-(4-nitrophenyl)-

Product 1

HCID 5354137Methyl 3-(4-nitrophenyl)-2-propenoate

Conditions

Temperature
25 °C

Procedure

A solution of p-nitrocinnamic acid (3.86 g, 20.0 mmol) in MeOH (50 mL) was treated with H2SO4 (2 mL) and was stirred at 25° C. for 24 h. Concentration afforded S31 (4.10 g, 19.8 mmol, 99%) as a yellow solid: 1H NMR (CDCl3, 500 MHz) 8.26 (d, 2H, J=8.4 Hz), 7.12 (d, 1H, J=16.1 Hz), 7.68 (d, 2H, J=8.8 Hz), 6.58 (d, 1H, J=16.1 Hz), 3.85 (s, 3H).

Workup

  1. concentrationConcentration
  2. customafforded S31 (4.10 g, 19.8 mmol, 99%) as a yellow solid

Sources & evidence

ORD record
ord-2d6371425109489396de1ea2680e66a5
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Linked notes

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