1-Propanol → 3-Ethoxy-4-hydroxyphenylacetic acid propyl ester

HRID 1744416Notes

Reaction equation

HRID 1744416 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].[CH2:5]([O:7][CH2:8][CH3:9])[CH3:6]>OS(O)(=O)=O>[CH2:1]([O:4][C:1](=[O:4])[CH2:2][C:3]1[CH:3]=[CH:2][C:1]([OH:4])=[C:5]([O:7][CH2:8][CH3:9])[CH:6]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 10311-Propanol2×HCID 3283Diethyl Ether

Product 1

HCID 112878593-Ethoxy-4-hydroxyphenylacetic acid propyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
90 °C

Procedure

Compound B3 (1.40 g, 5.87 mmol) was dissolved in an excess of 1-propanol (50 mL), concentrated H2SO4 (3 drops) was added, and the mixture was heated at 90° C. for ˜18 hours. The volume of 1-propanol was reduced under vacuum, then the mixture was diluted with diethyl ether, washed with saturated sodium bicarbonate solution (2×), distilled water (1×), brine (1×), dried over magnesium sulfate and solvent was removed under vacuum, giving 3-ethoxy-4-hydroxyphenylacetic acid propyl ester as a yellow oil.

Workup

  1. additionwas added
  2. washwashed with saturated sodium bicarbonate solution (2×)
  3. distillationdistilled water (1×), brine (1×)
  4. dry with materialdried over magnesium sulfate and solvent
  5. customwas removed under vacuum

Sources & evidence

ORD record
ord-dbdb85624260428abc1f786fe47cdce8
Source dataset
uspto-grants-2006_03
Patent number
US07015346B2

Reaction notes

Loading…