4-Hydroxybenzoic Acid → 2-Hydroxyethyl 4-hydroxybenzoate

HRID 1742720Notes

Reaction equation

HRID 1742720 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11]1[O:13][CH2:12]1>C(O)(C)C>[OH:13][CH2:12][CH2:11][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 6354Ethylene Oxide

Product 1

HCID 2679502-Hydroxyethyl 4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Into an autoclave, 138 parts by weight of p-hydroxybenzoic acid, 1 part by weight of Na2CO2 and 300 parts by weight of isopropanol were charged, and at 90° C., 66 parts by weight of ethylene oxide was added thereto, and the reaction was conducted. After the reaction, the mixture was cooled, and the precipitate was collected by filtration and recrystallized twice from water to obtain 55 parts by weight of p-hydroxylbenzoic acid-β-hydroxyethyl ester ##STR75## having a melting point of 141° C. The structure was confirmed by 1H-NMR.

Workup

  1. customAfter the reaction
  2. temperaturethe mixture was cooled
  3. filtrationthe precipitate was collected by filtration
  4. customrecrystallized twice from water

Sources & evidence

ORD record
ord-3c8ebd089d604ce08f822de1c4cb5e80
Source dataset
uspto-grants-1994_08
Patent number
US05340911

Reaction notes

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