Ethylene Glycol → 2-Hydroxyethyl 3,4,5-trihydroxybenzoate

HRID 411097Notes

Reaction equation

HRID 411097 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5](O)(=[O:15])[C:6]1[CH:14]=[C:12]([OH:13])[C:10]([OH:11])=[C:8]([OH:9])[CH:7]=1.[Na+].[Cl-]>OS(O)(=O)=O>[OH:3][CH2:2][CH2:1][O:4][C:5](=[O:15])[C:6]1[CH:14]=[C:12]([OH:13])[C:10]([OH:11])=[C:8]([OH:9])[CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 370Gallic AcidHCID 5234Sodium Chloride

Product 1

HCID 30178352-Hydroxyethyl 3,4,5-trihydroxybenzoateYield 28%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
90 °C

Procedure

A mixture consisting of ethylene glycol (105 g, 1.11 mol), gallic acid (28.5 g, 168 mmol), and concentrated H2SO4 (10 drops) was stirred at 90° C. overnight before mixing with ice water (1500 ml). Upon adding NaCl (100 g), the solution was extracted with ethyl acetate (150 ml×4). The combined organic portion was evaporated to dryness to obtain (m) (9.98 g, 28%). Proton-NMR spectral data (DMSO-d6), δ (ppm): 3.64 (t, HOCH2CH2, 2H), 4.15 (t, ArOCH2CH2, 2H), 6.93 (s, aromatic, 2H)

Workup

  1. extractionthe solution was extracted with ethyl acetate (150 ml×4)
  2. customThe combined organic portion was evaporated to dryness

Sources & evidence

ORD record
ord-5c67e1d8159b4cffb23138879e9755d0
Source dataset
uspto-grants-2003_05
Patent number
US06558572B2

Reaction notes

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