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

HRID 439641Notes

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

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 5N 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 in ether is taken up. After drying on sodium sulfate, it is evaporated to dryness in a vacuum. The title compound is obtained as solid. Yield: 15.21 g (78.3% of theory) Elementary analysis: Cld: C 68.02 H 7.26 Fnd: C 68.13 H 7.34

Workup

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

Sources & evidence

ORD record: ord-b3f98d0aa5e64607bc69e77bfceff0d3
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05514810

Reaction notes

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