ChemicalBook CAS DataBase List VanillylMandelic Acid Ethyl Ester

VanillylMandelic Acid Ethyl Ester synthesis

3synthesis methods

Product Name:VanillylMandelic Acid Ethyl Ester
CAS Number:52058-11-4
Molecular formula:C11H14O5
Molecular Weight:226.23

74-96-4 Synthesis

74-96-4
436 suppliers
$9.00/5g

55-10-7 Synthesis

55-10-7
125 suppliers
$19.00/250mg

52058-11-4
10 suppliers
$140.00/250mg

Yield:52058-11-4 77%

Reaction Conditions:

Stage #1: 4-hydroxy-3-methoxy-mandelic acidwith caesium carbonate in methanol;water; pH=7;
Stage #2: ethyl bromide in N,N-dimethyl-formamide at 20;

Steps:

Preparation of ethyl 4-hydroxy-3-methoxymandelate (7)

4-hydroxy-3-methoxymandelic acid 5 (2.52 mmol, 0.500 g) wasdissolved in 5 mL of a (10:1) MeOH/H2O mixture and then treated with20% aqueous Cs2CO3 to ajust the pH to 7. After removal of the solvent,6 mL of DMF was added to the dry residue. After 5 minutes,ethylbromide (3.02 mmol, 226 μL) was added and the mixture wasstirred for 96 h or until completion was shown by TLC (50:50EtOAc/hexanes). HCl 1N is then added and the ester is extracted with 3 portions of CH2Cl2. Theorganic layers were combined, washed with brine, dried with Na2SO4 and concentrated in vacuo,giving an oil which was purified by flash chromatography (50:50 EtOAc/hexanes), yielding0.438 g (77%) of 7 as a white solid. mp = 76-79 oC. 1H-NMR (500 MHz, CDCl3): δ = 1.24 (3H,t, J = 7.41), 3.88 (3H, s), 4.15-4.22 (1H, m), 4.23-4.30 (1H, m), 5.08 (1H, s), 5.75 (1H, br), 6.88-6.94 (3H, m). 13C-NMR (125 MHz, CDCl3): δ = 14.06, 55.93, 62.18, 72.73, 108.85, 114.38,119.93, 130.36, 145.81, 146.65, 173.86. IR (NaCl): νmax 3436, 1731, 1516, 1274, 1206, 1152,1031 cm-1. HPLC (Retention time, %): 7.63 min, >99%. HRMS (ESI-TOF, m/z): calcd forC24H30O3Na (M+Na)+ = 249.0733, found 249.0739.

References:

Cardinal, Sébastien;Voyer, Normand [Tetrahedron Letters,2013,vol. 54,# 38,p. 5178 - 5180] Location in patent:supporting information

64-17-5 Synthesis