Benzene hexane → 2-Methyl-5-nitrobenzyl acetate

HRID 1388085

Reaction equation

HRID 1388085 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[CH3:6][C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=1[CH2:9]Cl.CCCCCC.C1C=CC=CC=1>C(O)(=O)C>[C:1]([O:4][CH2:9][C:8]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:7]=1[CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 110624Benzene hexaneHCID 1879522-(Chloromethyl)-1-methyl-4-nitrobenzeneHCID 517045Sodium Acetate

Product 1

HCID 129407612-Methyl-5-nitrobenzyl acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

A slurry of anhydrous sodium acetate (60.0 g; 0.73 mol) in acetic acid (400 ml) is stirred and 2-methyl-5-nitrobenzyl chloride (45.3 g; 0.24 mol) added. The resulting reaction mixture is heated to reflux and is heated overnight at 115° C., after which time tlc (silica gel; 75/25 hexane/benzene) indicates that no starting material is present. The mixture is cooled down, concentrated in vacuo, and diluted with water. The precipitated solid (48.9 g; 95.8%) is collected and dried. A sample recrystallized from hexane has a melting point of 52°-53.5° C.

Workup

  1. customThe resulting reaction mixture
  2. temperatureis heated
  3. temperatureto reflux
  4. temperatureThe mixture is cooled down
  5. concentrationconcentrated in vacuo
  6. additiondiluted with water
  7. customThe precipitated solid (48.9 g; 95.8%) is collected
  8. customdried
  9. customA sample recrystallized from hexane

Sources & evidence

ORD record
ord-25feafc9070146f49ae4c1ce2acbaf1c
Source dataset
uspto-grants-1984_02
Patent number
US04430114

Linked notes

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