ChemicalBook CAS DataBase List DL-3,4-DIHYDROXYPHENYL GLYCOL

DL-3,4-DIHYDROXYPHENYL GLYCOL synthesis

9synthesis methods

Product Name:DL-3,4-DIHYDROXYPHENYL GLYCOL
CAS Number:28822-73-3
Molecular formula:C8H10O4
Molecular Weight:170.16

29477-54-1
48 suppliers
inquiry

28822-73-3
104 suppliers
$140.00/10mg

Yield:28822-73-3 80%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 20; under 2585.81 Torr; for 9 h;

Steps:

3,4-dihydroxyphenylglycol (DHPG, 7)

A solution of 6 (1.4 g, 8.33 mmol) in methanol (80 mL)was hydrogenated in the presence of 10% Pd/C (100 mg), under a pressure of 50 psi, at roomtemperature for 9 h. The resulting mixture was filtered through a Celite pad, and the filtrate wasevaporated to dryness. Treatment with activated charcoal in hot methanol and filtration through aCelite pad afforded the title compound practically pure (1.13 mg, 80%). For analytical reasons, a smallamount was quickly purified (due to stability reasons) by column chromatography (silica gel) usinga mixture of cyclohexane/ethyl acetate 1/4 as the eluent. 1H NMR (600 MHz, CD3OD) δ: 6.83 (d, 1, J =2.0 Hz, H-2), 6.74 (d, 1, J = 8.2 Hz, H-5), 6.68 (d, 1, J = 8.2 Hz, H-6), 4.55 (t, 1, J = 6.1 Hz, CHCH2), 3.58(d, 2, J = 6.0 Hz, CHCH2). 13C NMR (151 MHz, CD3OD) δ: 146.07 (C-3), 145.72 (C-4), 134.72 (C-1), 118.98(C-6), 116.11 (C-5), 114.64 (C-2), 75.70 (CHCH2), 68.69 (CHCH2). (-) ESI QqToF (m/z): Calcd. for C8H9O4-: [M - H]- 169.0506, found 169.0512.

References:

Kalampaliki, Amalia D.;Giannouli, Vassiliki;Skaltsounis, Alexios-Leandros;Kostakis, Ioannis K. [Molecules,2019,vol. 24,# 18,art. no. 3239]