Hydrochloric Acid → 2-(2-Methoxyethoxy)ethyl 4-hydroxybenzoate

HRID 1439923Notes

Reaction equation

HRID 1439923 reaction equation
[Na].[OH:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.Cl.[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19]CO>>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7456MethylparabenHCID 8134Diethylene Glycol Monomethyl EtherHCID 5360545Sodium

Product 1

HCID 189851042-(2-Methoxyethoxy)ethyl 4-hydroxybenzoate

Conditions

Temperature
130 °C

Procedure

In a first step, an amount of 1 g (43 mmol) of sodium was dissolved in 25 of ml 2-(2-methoxyethoxy)ethanol. To the resulted solution an amount of 3 g (22 mmol) of methyl 4-hydroxybenzoate was added and the mixture was heated to 130° C. for 24 hours; after cooling to room temperature, it was acidified with a hydrochloric acid solution (3N) and extracted with ethyl acetate. The removal of the solvent under reduced pressure and column chromatography of the residue (silica gel, hexane:ethyl acetate 3:1) afforded 2-(2-methoxyethoxy)ethyl 4-hydroxybenzoate, in the form of a colourless oil in essentially quantitative yield.

Workup

  1. temperatureafter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe removal of the solvent under reduced pressure and column chromatography of the residue (silica gel, hexane:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-2de1a41887514c1786b64dfc86c398a8
Source dataset
uspto-grants-1996_03
Patent number
US05496854

Reaction notes

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