ChemicalBook CAS DataBase List 2,5-BIS-BENZYLOXY-BENZOIC ACID

2,5-BIS-BENZYLOXY-BENZOIC ACID synthesis

5synthesis methods

Product Name:2,5-BIS-BENZYLOXY-BENZOIC ACID
CAS Number:67127-91-7
Molecular formula:C21H18O4
Molecular Weight:334.37

Benzoic acid, 2,5-bis(phenylmethoxy)-, phenylmethyl ester

78283-37-1
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Yield:67127-91-7 91%

Reaction Conditions:

with sodium hydroxide in 1,4-dioxane;methanol;water; for 14 h;Reflux;

Steps:

2,5-Dibenzyloxybenzoic acid (13)

A solution of 1.0 g (2.4 mmol) of ester 25 and 0.19 g (4.7 mmol) of sodium hydroxide in 15 mL of methanol, dioxane, and water (1:1:1) was stirred under reflux for 14 h, cooled to 25^oC, and most of the organic solvents were removed from a rotary evaporator. The residue was diluted with water, acidified with 1 N HCl, extracted twice with ethyl acetate (50 mL), and the ethyl acetate layers were combined, washed with water and brine, dried (MgSO₄), concentrated, and column chromatographed using a mixture of hexane and ethyl acetate (1:1) as eluent to give 0.72 g (91% yield) of compound 13.¹⁵ ¹H NMR δ 11.06 (s, 1 H), 7.81 (d, J = 3.1 Hz, 1 H), 7.43 - 7.32 (m, 10 H), 7.17 (dd, J = 9.0, 3.1 Hz, 1 H), 7.07 (d, J = 9.0 Hz, 1 H), 5.26 (s, 2 H), 5.08 (s, 2 H); ¹³C NMR δ 165.3, 153.9, 151.9, 136.6, 134.6, 129.4, 129.4, 128.8, 128.4, 128.2, 127.8, 123.0, 119.0, 117.8, 115.1, 73.2, 70.9.

References:

Thapa, Mahendra;Kim, Yunjeong;Desper, John;Chang, Kyeong-Ok;Hua, Duy H. [Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,# 1,p. 353 - 356] Location in patent:supporting information; experimental part