1-Propanol → Propyl 4-hydroxy-3-methoxyphenylacetate

HRID 1744417Notes

Reaction equation

HRID 1744417 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

HCID 10311-PropanolHCID 16928Homovanillyl alcohol

Product 1

HCID 104310Propyl 4-hydroxy-3-methoxyphenylacetate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

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.

Workup

  1. customthe 1-propanol was removed under reduced pressure
  2. additionthe resulting oil was diluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate solution
  4. distillationdistilled water
  5. dry with materialThe solution was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1852d8433e5d457aba05b0bd09792e6f
Source dataset
uspto-grants-2006_03
Patent number
US07015346B2

Reaction notes

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