Nitroethane → Methyl 2-hydroxy-3-(2-nitro-1-propenyl)benzoate

HRID 1761927Notes

Reaction equation

HRID 1761927 reaction equation
[CH:1]([C:3]1[C:4]([OH:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[N+:14]([CH2:17][CH3:18])([O-:16])=[O:15].N1CCCCC1>C1(C)C=CC=CC=1>[OH:13][C:4]1[C:3]([CH:1]=[C:17]([N+:14]([O-:16])=[O:15])[CH3:18])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 8082PiperidineHCID 345559Methyl 3-formyl-2-hydroxybenzoate

Product 1

HCID 53867347Methyl 2-hydroxy-3-(2-nitro-1-propenyl)benzoateYield 81.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.90 g of methyl 3-formyl-2-hydroxybenzoate, 3.0 g of nitroethane, 0.15 ml of piperidine and 30 ml of toluene is refluxed overnight while removing water. The reaction mixture is poured into ice-water and the aqueous mixture is extracted with ethyl acetate. The extract is washed successively with 10% hydrochloric acid and an aqueous saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is recrystallized from methanol to give 2.05 g of methyl 2-hydroxy-3-(2-nitro-1-propenyl)benzoate.

Workup

  1. temperatureis refluxed overnight
  2. customwhile removing water
  3. additionThe reaction mixture is poured into ice-water
  4. extractionthe aqueous mixture is extracted with ethyl acetate
  5. washThe extract is washed successively with 10% hydrochloric acid
  6. dry with materialan aqueous saturated sodium chloride solution, dried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-2f99eea561ca41b08522cbc9185f4cad
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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