3-(4-Hydroxyphenyl)propionic acid → Benzenepropanoic acid, 4-hydroxy-, methyl ester

HRID 250826Notes

Reaction equation

HRID 250826 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.[C:13](=O)([O-])O.[Na+]>CO.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

5

Reactant 2

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterYield 92%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

15 g (0.09 mol, 1 eq) of 3-(4-hydroxyphenyl)propanoic acid are dissolved in 50 ml of methanol and 4 drops of sulfuric acid are added. The reaction mixture is stirred for 16 hours at room temperature. The reaction is stopped by addition of 50 mL of saturated sodium hydrogen carbonate solution and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 14.9 g of methyl 3-(4-hydroxyphenyl)propanoate are obtained. Yield=92%

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-1ded33c10561458c8618c997673e643e
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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