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

HRID 1981647Notes

Reaction equation

HRID 1981647 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 3A molecular sieves. The solution was refluxed for 72 hours and the sieve 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. temperatureThe solution was refluxed for 72 hours
  2. customThe reaction medium was then evaporated to an oil which
  3. dissolutionwas dissolved in 100 mL toluene
  4. extractionextracted with 3×100 mL water
  5. dry with materialThe toluene phase was dried over magnesium sulfate
  6. additiontreated with activated charcoal
  7. customevaporated

Sources & evidence

ORD record
ord-0407e3df328346a6af8e88b91a760720
Source dataset
uspto-grants-1986_06
Patent number
US04593119

Reaction notes

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