Acetone → Dimethyl Sulfate

HRID 2103061Notes

Reaction equation

HRID 2103061 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[C:4]([CH3:12])[C:3]=1[OH:13].[C:14]([O-])([O-])=O.[K+].[K+].CC(C)=O.[CH3:24][O:25][S:26]([O:29][CH3:30])(=[O:28])=[O:27]>C(OC(=O)C)C.O>[CH3:14][O:13][C:3]1[C:2]([CH3:1])=[C:7]([CH3:8])[C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH3:12].[CH3:24][O:25][S:26]([O:29][CH3:30])(=[O:28])=[O:27]

Participants

8

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 133312472,3,6-Trimethyl-4-nitrophenol

Product 2

HCID 6497Dimethyl SulfateYield 5%HCID 224085124-Nitro-2,3,6-trimethylanisole

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2,3,6-Trimethyl-4-nitrophenol (2.2 g) and K2CO3 (4.0 g) were added to a flask, to which was slowly added acetone (35 mL), followed by dimethylsulfate (2.09 mL) at room temperature. The suspension was then refluxed for 2.5 hours. After it cooled down, 20 mL water was added and stirred for 15 min. The mixture was taken up by water and ethylacetate and the organic phase was washed with brine, dried and evaporated to give 2-methoxy-1,3,4-trimethyl-5-nitrobenzene as an oil (2.3 g, which still contained 5% dimethylsulfate). 1H-NMR, (300 MHz, CDCl3) δ=7.532, (s, 1H), 3.723, (s, 3H), 2.373, (s, 3H), 2.307 (s, 3H), 2.273 (s, 3H) ppm.

Workup

  1. temperatureThe suspension was then refluxed for 2.5 hours
  2. temperatureAfter it cooled down
  3. washthe organic phase was washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-8a5831d684d04dc1ad68b4e7707c9400
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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