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

HRID 1731768Notes

Reaction equation

HRID 1731768 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 heated to reflux for 72 hours and the sieves were exchanged at 24 hours 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 heated
  3. temperatureto reflux for 72 hours
  4. customThe reaction medium was then evaporated to an oil which
  5. dissolutionwas dissolved in 100 ml toluene
  6. extractionextracted with 3×100 ml water
  7. dry with materialThe toluene phase was dried over magnesium sulfate
  8. additiontreated with activated charcoal
  9. customevaporated

Sources & evidence

ORD record
ord-2bddcb73929c43bda1c7175fb530f50f
Source dataset
uspto-grants-1986_11
Patent number
US04623652

Reaction notes

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