Methanol → HCID 18694844, compound

HRID 1871060Notes

Reaction equation

HRID 1871060 reaction equation
[CH3:1]O.[Cl:3][C:4]1[C:12]([CH3:13])=[C:11]([O:14][CH3:15])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].S(=O)(=O)(O)O>C1C=CC=CC=1>[Cl:3][C:4]1[C:12]([CH3:13])=[C:11]([O:14][CH3:15])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH3:1])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 11458315HCID 11458315, compound

Product 1

HCID 18694844HCID 18694844, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 150 ml methanol, was dissolved 2-chloro-4-methoxy-3-methylbenzoic acid in an amount of 16.6 g (0.0832 mole), and the resulting solution was stirred for 18 hours under reflux and heating following to the addition of concentrated sulfuric acid in an amount of 1.0 g into the solution. The residue obtained by distillating out the solvent under reduced pressure was dissolved in benzene, washed with 3% aqueous solution of sodium hydrogencarbonate and subsequently with saturated saline solution and dried with anhydrous magnesium sulfate. After distillating out the solvent in the solution under reduced pressure, the crystals remained were washed with methanol to obtain methyl 2-chloro-4-methoxy-3-methylbenzoate in an amount of 13.5 g. The yield was 76.0%.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. customThe residue obtained
  4. washwashed with 3% aqueous solution of sodium hydrogencarbonate and subsequently with saturated saline solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. washthe crystals remained were washed with methanol

Sources & evidence

ORD record
ord-8e306f0a11934a8cabe62afcd83d2c45
Source dataset
uspto-grants-2000_08
Patent number
US06100421

Reaction notes

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