Benzene → 3-Nitrophenyl acetate

HRID 1110079Notes

Reaction equation

HRID 1110079 reaction equation
[Mg].[N+:2]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].C1C=CC=CC=1.[C:18](Cl)(=[O:20])[CH3:19]>CCOCC>[C:18]([O:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6367Acetyl chlorideHCID 111373-NitrophenolHCID 5462224Magnesium

Product 1

HCID 152073-Nitrophenyl acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

Magnesium turnings (1.2 g) were added to a solution of m-nitrophenol (6.95 g), benzene (40 ml) and acetyl chloride (4 g) and the solution heated for 1 hour at 90° C. The reaction mixture was diluted with ether and decanted from unreacted magnesium. The ether layer was washed successively with water, dilute NaOH and water. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to give m-nitrophenyl acetate. m.p. 55°-56° C. 1H n.m.r. δ2.4, s, 3H, H3C--CO--; 7.4-8.4, m, 4H, ArH. υmax 1770 cm-1.

Workup

  1. customdecanted from unreacted magnesium
  2. washThe ether layer was washed successively with water, dilute NaOH and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a54a321eaf9a4e88a8c07bfb4a7f7fb9
Source dataset
uspto-grants-1994_06
Patent number
US05324750

Reaction notes

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