propyl 4-hydroxy-3-methoxybenzoate synthesis

Yield:6273-95-6 64.3%

Reaction Conditions:

with acetyl chloride at 60; for 48 h;

Steps:

1.1.1. Propyl vanillate (3)

Vanillic acid(2.50 g, 14.9 mmol) and acetyl chloride (250 μl, 2.8 mmol) weredissolved in 1-propanol (49.75 ml), and the reaction mixture was stirred at 60°C. After 48 h, thereaction mixture was evaporated to dryness. The resulting residue was purifiedby a Wakogel C-200 (Φ 3.0 x 23.0 cm), eluted with hexane/ethyl acetate (8:2, v/v), and thenrecrystallized with hexane to yield propyl vanillate (2.01 g, 64.3%). ¹HNMR (CD₃OD, 600 MHz) δ: 1.06 (3H, t, J = 7.2 Hz); 1.81 (2H, sext,J = 7.2 Hz); 3.93 (3H, s); 4.26 (2H,t, J = 6.6 Hz); 6.88 (1H, d, J = 7.8 Hz); 7.57 (1H, d, J = 1.8 Hz); 7.59 (1H, dd, J = 1.8, 8.4 Hz). ¹³C NMR (CD₃OD,150 MHz) δ: 10.57, 22.99, 56.15, 67.16, 113.21, 115.68,122.55, 124.70, 148.51, 152.57, 168.01. ESI-HRMS [M-H]^-: calcd. forC₁₁H₁₃O₄: 209.0819, found 209.0811. HPLC: rt7.8 min, 99.2% purity.

References:

Ishimata, Nao;Ito, Hideyuki;Tai, Akihiro [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 15,p. 3533 - 3536] Location in patent:supporting information