Nitromethane → HCID 22168455, compound

HRID 1375675Notes

Reaction equation

HRID 1375675 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][N+:11]([O-:13])=[O:12].[OH-].[K+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH2:10][N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14797Potassium HydroxideHCID 765833-Bromobenzaldehyde

Product 1

HCID 22168455HCID 22168455, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromobenzaldehyde (18.5 g, 100 mmol) in MeOH (100 mL) was added MeNO2 (12.2 g, 200 mmol) at 0° C. followed by addition of KOH (11.2 g, 200 mmol). After 2 hours, MeOH was removed in vacuo and the resulting mixture was partitioned between ethyl acetate and water. Ethyl acetate extracts were dried over MgSO4 and concentrated to give 20 g crude mixture. This crude mixture was dissolved in AcOH (200 mL), to which CrO3 (12.0 g, 120 mmol) was added. Acetic acid was removed under vacuo after 2 hours and water (200 mL) was added and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over MgSO4, filtered and then concentrated under vacuo. dichloromethane (20 mL) was added and the titled compound (8.5 g, 35% for 2 steps) was precipitated out and collected by filtration.

Workup

  1. customMeOH was removed in vacuo
  2. customthe resulting mixture was partitioned between ethyl acetate and water
  3. dry with materialEthyl acetate extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-494689226de749728667982519ce01e5
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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