Dimethyl Sulfate → Methyl 4-isopropoxy-2-methoxybenzoate

HRID 2293538Notes

Reaction equation

HRID 2293538 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(=O)CC>[CH:13]([O:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:1][CH3:16])[CH:11]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 23244891Methyl 2-hydroxy-4-isopropoxybenzoate

Product 1

HCID 21477058Methyl 4-isopropoxy-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A 1.60 g portion of methyl 2-hydroxy-4-isopropoxybenzoate was dissolved in 30 ml of 2-butanone, 1.60 g of potassium carbonate and 1.1 ml of dimethyl sulfate were added, followed by 12 hours of heating under reflux. After completion of the reaction, the solvent was evaporated, the resulting residue was suspended in chloroform, insoluble matter was removed by filtration through celite, and the solvent was again evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-2:1) to give 1.70 g of methyl 4-isopropoxy-2-methoxybenzoate.

Workup

  1. temperatureof heating
  2. temperatureunder reflux
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated
  5. custominsoluble matter was removed by filtration through celite
  6. customthe solvent was again evaporated
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-2:1)

Sources & evidence

ORD record
ord-af0a816398bb4f319ccbe8b9160c84b4
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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