3-(4-Hydroxyphenyl)propanal → 3-(4-Hydroxyphenyl)propionic acid

HRID 2415429Notes

Reaction equation

HRID 2415429 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=[O:11])=[CH:4][CH:3]=1.CC(C)=[O:14].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:14])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 119574273-(4-Hydroxyphenyl)propanalHCID 131709961Jones' reagent

Product 1

HCID 103943-(4-Hydroxyphenyl)propionic acidYield 63.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

0.79 g (5.19 mmoles) of 3-(4-hydroxyphenyl)-1-propanal were dissolved in acetone (20 ml) and Jones reagent (chromic anhydride in sulphuric acid) (8 ml) was added to it drop by drop until the yellow-brown colour persisted. The solution was stirred for one hour at 0° C. The excess reagent was destroyed with methanol and the solution was filtered and evaporated at reduced pressure. The residue was extracted in ethyl acetate, dried over anhydrous sodium sulphate and concentrated, diving an impure residue (0.6470 g), which was chromatographed over silica gel, obtaining 0.545 g (63.1% yield) of 3-(4-hydroxyphenyl) propionic acid. Recrystallisation in methanol gave m.p.=121° C.

Workup

  1. customThe excess reagent was destroyed with methanol
  2. filtrationthe solution was filtered
  3. customevaporated at reduced pressure
  4. extractionThe residue was extracted in ethyl acetate
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customdiving an impure residue (0.6470 g), which was chromatographed over silica gel

Sources & evidence

ORD record
ord-92d91c0ded25429cb85ff1f1dc9d261b
Source dataset
uspto-grants-2004_11
Patent number
US06818780B2

Reaction notes

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