Hydrochloric Acid → 1-Ethoxy-3-(2-nitroethyl)benzene

HRID 1784413Notes

Reaction equation

HRID 1784413 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].[CH2:5]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[CH3:6].[OH-].[Na+].Cl>CO.O>[CH2:5]([O:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:10]([CH2:11][CH2:4][N+:1]([O-:3])=[O:2])[CH:9]=1)[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 899083-Ethoxybenzaldehyde

Product 1

HCID 688305181-Ethoxy-3-(2-nitroethyl)benzeneYield 37.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of nitromethane (0.36 mL, 6.7 mmol) and 3-ethoxy-benzaldehyde (1 g, 6.7 mmol) in methanol (1.4 mL) was cooled to −10° C. To this mixture sodium hydroxide (0.28 g in 1 mL water) was added dropwise. The temperature during addition was maintained around 10° C. After 1 hour a yellow precipitate formed and water (5 mL) was added. The resulting solution was added to HCl (4M, 3 mL). The precipitate that formed was filtered off and washed with water. Purification by chromatography on silica, eluting with 1 to 15% ethyl acetate in hexane, gave the subtitled compound as a yellow solid (0.49 g). 1H NMR δ (CDCl3) 1.40-1.48 (3H, t), 4.014.13 (2H, q), 6.97-7.06 (2H, m), 7.09-7.15 (1H, d), 7.30-7.40 (1H, t), 7.53-7.62 (1H, d), 7.91-8.00 (1H, d).

Workup

  1. additionThe temperature during addition
  2. temperaturewas maintained around 10° C
  3. customAfter 1 hour a yellow precipitate formed
  4. customThe precipitate that formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customPurification by chromatography on silica
  8. washeluting with 1 to 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7468f6f5425a4ab6ada581796ad9d8dc
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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