Dimethyl Sulfate → Methyl 4-methoxysalicylate

HRID 256337

Reaction equation

HRID 256337 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8].[C:13](=O)(O)[O-].[Na+].S(OC)(OC)(=O)=O>CC(C)=O.CCOCC.C1(C)C=CC=CC=1>[CH3:13][O:8][C:7](=[O:9])[C:6]1[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=1)[OH:12]

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 752314-Methoxysalicylic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 79523Methyl 4-methoxysalicylateYield 98,858.797%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-methoxysalicylic acid (Aldrich) (178.1 g, 1.06 mmole) sodium bicarbonate (89 g, 1.06 mole), and dimethyl sulfate (133.6 g, 1.06 mole) in acetone (2 l) is refluxed with stirring under nitrogen for 20 hours. The mixture is cooled, filtered, and the acetone is removed under reduced pressure to yield an oily residue. The residue is taken up in ether (1.8 l) and toluene (0.50 l). The extracts are washed with sodium bicarbonate solution, water, dried over sodium sulfate, and concentrated to give a syrup (190.9 g). Recrystallization from hexane gives 172.7 g (89.5%) of analytically pure solid, mp 49°-50° C.

Workup

  1. temperatureis refluxed
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customthe acetone is removed under reduced pressure
  5. customto yield an oily residue
  6. washThe extracts are washed with sodium bicarbonate solution, water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f7f85d8a445d4379b1ab9d2dff21c91b
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Linked notes

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