Acetone → Methyl 3-methoxy-4-nitrobenzoate

HRID 2246064Notes

Reaction equation

HRID 2246064 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])C(O)=O.[C:14]([O-:17])([O-])=[O:15].[K+].[K+].COS([O:25][CH3:26])(=O)=O.[CH3:27]C(C)=O>>[CH3:27][O:17][C:14](=[O:15])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([O:25][CH3:26])[CH:3]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 692653-Hydroxy-4-nitrobenzoic acid

Product 1

HCID 287308Methyl 3-methoxy-4-nitrobenzoate

Procedure

A 5-L, 3-necked, round-bottomed flask fitted with an overhead stirrer and a 250 mL addition funnel was charged with 3-hydroxy-4-nitrobenzoic acid (122 g, 0.66 mol), acetone (reagent grade, 1.5 L) and powdered K2CO3 (185 g). To this stirred suspension dimethylsulfate (127 mL) was added drop-wise. The suspension was stirred at room temperature for 18 h and filtered. The filtrate was concentrated under reduced pressure to about half the volume (ca 750 mL), transferred to a 3-L beaker and water (1-L) was added with stirring. The precipitated product was collected by filtration and dried in vacuum to obtain the title compound 32 as a white crystalline solid mp 87-88° C. 1H NMR (400 MHz, CDCl3) δ: 7.77 (d, 1H), 7.68 (d, 1H), 7.63 (d, 1H), 3.94 (s, 3H), 3.90 (s, 3H). MS (ES) m/z212.1 (MH)+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure to about half the volume (ca 750 mL)
  3. additionwas added
  4. stirringwith stirring
  5. filtrationThe precipitated product was collected by filtration
  6. customdried in vacuum

Sources & evidence

ORD record
ord-016c9c035a7f4ac1855154f1ed52647c
Source dataset
uspto-grants-2010_03
Patent number
US07687494B2

Reaction notes

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