ChemicalBook CAS DataBase List 4-(benzyloxy)-3-cyanobenzoic acid

4-(benzyloxy)-3-cyanobenzoic acid synthesis

5synthesis methods

Product Name:4-(benzyloxy)-3-cyanobenzoic acid
CAS Number:946007-61-0
Molecular formula:C15H11NO3
Molecular Weight:253.25

Benzoic acid, 3-cyano-4-(phenylmethoxy)-, phenylmethyl ester

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Yield:946007-61-0 93%

Reaction Conditions:

Stage #1: benzyl 4-(benzyloxy)-3-cyanobenzoatewith sodium hydroxide;water in methanol at 20; for 2 h;
Stage #2: with hydrogenchloride in water; pH=2;

Steps:

1

To a solution of compound 17 (3.5 g, 10.0 mmol) in methanol (70 mL), aq. solution of 4N NaOH (1.2 g, 30.0 mmol) is added. The solution is evaporated after stirring at room temperature for 2 h. The residue is dissolved in water and insolubles are filtered off. The filtrate is carefully neutralized with cone. HCl (pH 2), the precipitated white solid is filtered and washed with cold water and dried to complete dryness. Yield 2.4 g, 93%; mp 203-207 ⁰C; ¹HNMR (400 MHz, MeOH-d₄) δ 5.27 (s, 2H), 7.25-7.39 (m, 4H), 7.45-7.46 (m, 2H), 8.16-8.19 (m, 2H); ¹³CNMR (101 MHz, MeOH-d₄) δ 70.92, 101.87, 112.84, 115.13, 123.90, 127.23, 128.12, 128.42, 135.28, 135.59, 136.03, 163.48, 166.23; IR (Neat, cm^"1) 3045.0, 2230.0, 1708.7, 1605.6, 1502.3.

References:

WO2008/92072,2008,A2 Location in patent:Page/Page column 13-14