1-Propanol → Propyl 4-hydroxy-3-methoxyphenylacetate
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][C:3]=1[O:11][CH3:12].[CH2:13]([OH:16])[CH2:14][CH3:15]>S(=O)(=O)(O)O>[CH2:13]([O:16][C:7](=[O:8])[CH2:6][C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([O:11][CH3:12])[CH:4]=1)[CH2:14][CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
4-Hydroxy-3-methoxyphenethyl alcohol (Sigma-Aldrich) was dissolved in anhydrous 1-propanol. To this solution ˜5 drops of concentrated sulphuric acid were added and the solution was heated at 100° C. for 3-5 hours in a pressure tube. When the reaction was complete, the 1-propanol was removed under reduced pressure, the resulting oil was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution, distilled water, and then brine. The solution was dried over magnesium sulfate and filtered and the solvent was removed under reduced pressure, giving 15-A as a red oil in almost quantitative yield.