Nitromethane → o-Chloro-beta-nitrostyrene

HRID 1843847Notes

Reaction equation

HRID 1843847 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:10]([CH3:13])([O-:12])=[O:11].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:13][N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 69962-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 98458o-Chloro-beta-nitrostyreneYield 75.73%

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, 2-chloro-benzaldehyde (5 g, 35.7142 mmol) in ethanol (161 mL) was reacted with nitro methane (1.93 mL, 35.7142 mmol) and 10N NaOH (1.35 g, 33.9607 mmol). The resulting mixture was stirred at 0° C. for 1 hr to afford 4.5 g of the product (75.73% yield).

Workup

  1. customan analogous reaction procedure

Sources & evidence

ORD record
ord-ee1a3d0c707d44a88e5063cc0b03e640
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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