Methanol → Methyl 3-hexyl-4-methoxybenzoate

HRID 850439Notes

Reaction equation

HRID 850439 reaction equation
[CH2:1]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:10]([OH:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:18]O>S(=O)(=O)(O)O.O>[CH2:1]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:10]([O:12][CH3:18])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 887MethanolHCID 193634153-Hexyl-4-methoxybenzoic acid

Product 1

HCID 19363353Methyl 3-hexyl-4-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

A crude product of 3-hexyl-4-methoxybenzoic acid and methanol (4 ml) were mixed. To this solution was added conc. sulfuric acid (2 drops), and the mixture was refluxed under heating for 20 hours. Water (10 ml) was added and methanol was evaporated under reduced pressure. The aqueous layer was extracted 3 times with ethyl acetate (20 ml). The organic layers were combined, and washed 3 times with saturated brine (20 ml). This solution was dried over anhydrous magnesium sulfate, and the drying agent was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (hexane/ethyl acetate=10/1) to give methyl 3-hexyl-4-methoxybenzoate (96.2 g) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 20 hours
  3. custommethanol was evaporated under reduced pressure
  4. extractionThe aqueous layer was extracted 3 times with ethyl acetate (20 ml)
  5. washwashed 3 times with saturated brine (20 ml)
  6. dry with materialThis solution was dried over anhydrous magnesium sulfate
  7. filtrationthe drying agent was filtered off
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe obtained residue was purified by column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-1b841f5488f7483ab27d1291d0f7dac1
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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