Nitromethane → 3-Methoxy--nitrostyrene

HRID 1843842Notes

Reaction equation

HRID 1843842 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[N+:11]([CH3:14])([O-:13])=[O:12].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([CH:6]=[CH:14][N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 115693-MethoxybenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 2614113-Methoxy--nitrostyreneYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Using an analogous reaction procedure and workup as described in Example 1, step 1, 3-methoxy-benzaldehyde (16.0 g, 118.518 mmol) in ethanol (160 mL) was reacted with nitro methane (7.0 mL, 118.518 mmol) and 10N NaOH (4.7 g, 118.518 mmol). The resulting mixture was stirred at 0° C. for 4 hours to afford 10.5 g of the product (49% yield).

Workup

  1. customan analogous reaction procedure

Sources & evidence

ORD record
ord-ffc931f9d2e64cd69826c3f345591227
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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