Nitroethane → 2-Hydroxy-4-methoxybenzonitrile

HRID 1582470Notes

Reaction equation

HRID 1582470 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])(=O)C.[Na+].[N+:17](CC)([O-])=O>C(O)(=O)C>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:17]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 114236802-Hydroxy-4-methoxybenzonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-hydroxy-4-methoxybenzaldehyde (25.0 g, 164 mmol), sodium acetate (26.4 g, 322 mmol), nitroethane (23 g, 307 mmol) in acetic acid (45 mL) was heated at reflux for 6 h. The mixture was then cooled to room temperature and poured onto ice water. The solids were filtered off, washed with water and dried. Recrystallization of the crude solid in ethyl acetate gave 2-hydroxy-4-methoxy-benzonitrile as a brown solid (15.9 g, 65%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. additionpoured onto ice water
  4. filtrationThe solids were filtered off
  5. washwashed with water
  6. customdried
  7. customRecrystallization of the crude solid in ethyl acetate

Sources & evidence

ORD record
ord-31382ed39c264e588d85a054dc733aed
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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