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

HRID 1013566Notes

Reaction equation

HRID 1013566 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][C:6]=1[O:15][CH2:16][CH3:17])(=O)C.[CH2:18](O)[CH2:19][CH3:20]>OS(O)(=O)=O.C(OCC)C>[CH2:18]([O:14][C:12](=[O:13])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[C:6]([O:15][CH2:16][CH3:17])[CH:7]=1)[CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 10311-Propanol2×HCID 20778780(4-Acetoxy-3-ethoxyphenyl)-acetic acid

Product 1

HCID 112878593-Ethoxy-4-hydroxyphenylacetic acid propyl ester

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

Intermediate 4 (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 intermediate 5 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-7e79e4fff7ae42b1a1842d82769bcfe0
Source dataset
uspto-grants-2011_07
Patent number
US07981931B2

Reaction notes

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