Methanol → Benzenepropanoic acid, 4-hydroxy-, methyl ester

HRID 2166517Notes

Reaction equation

HRID 2166517 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH3:13]O>S(=O)(=O)(O)O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 103943-(4-Hydroxyphenyl)propionic acid

Product 1

HCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 17 gm (0.1 mole) of 3-(4-hydroxyphenyl)propionic acid in 500 mL methanol and 2 mL concentrated sulfuric acid was placed in a Soxhlet extractor charged with 3 A molecular sieves. The solution was refluxed for 72 hours and the sieves were exchanged at 24 hour intervals. The reaction medium was then evaporated to an oil which was dissolved in 100 mL toluene and extracted with 3×100 mL water. The toluene phase was dried over magnesium sulfate, treated with activated charcoal and evaporated to provide 15 gm (80%) of a clear oil. The NMR spectrum was consistent with the assigned structure and this material was utilized directly in the next reaction step.

Workup

  1. additioncharged with 3 A molecular sieves
  2. temperatureThe solution was refluxed for 72 hours
  3. customThe reaction medium was then evaporated to an oil which
  4. dissolutionwas dissolved in 100 mL toluene
  5. extractionextracted with 3×100 mL water
  6. dry with materialThe toluene phase was dried over magnesium sulfate
  7. additiontreated with activated charcoal
  8. customevaporated

Sources & evidence

ORD record
ord-8d56cf1b764a4952acebd8f903039502
Source dataset
uspto-grants-1983_06
Patent number
US04387103

Reaction notes

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