Diethyl Sulfate → 3-(4-Ethoxyphenyl)propanoic acid

HRID 1489931Notes

Reaction equation

HRID 1489931 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].S(OCC)(O[CH2:19][CH3:20])(=O)=O>O>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1)[CH3:20]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 14798Sodium Hydroxide

Product 1

HCID 2919853-(4-Ethoxyphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

16.62 g (100 mmol) of 3-(4-hydroxyphenyl)-propionic acid is dissolved with stirring and covering with argon in 45 ml (225.0 mmol) of 5 N sodium hydroxide solution, and 15.73 g (100 mmol), (98%) of diethyl sulfate is instilled quickly so that the temperature does not exceed 40° C. (water cooling). After completion of the addition, it is heated for 30 more minutes to 100° C. After the cooling, it is extracted with diethyl ether, then acidified with sulfuric acid to pH 4 and the precipitated compound is taken up in ether. After drying on sodium sulfate, it is evaporated to dryness in a vacuum. The title compound is obtained as solid.

Workup

  1. customdoes not exceed 40° C.
  2. additionAfter completion of the addition, it
  3. extractionAfter the cooling, it is extracted with diethyl ether
  4. customAfter drying on sodium sulfate, it
  5. customis evaporated to dryness in a vacuum

Sources & evidence

ORD record
ord-955ce0cffa0c4212b9430fe011815456
Source dataset
uspto-grants-1997_10
Patent number
US05679852

Reaction notes

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