4'-(BENZYLOXY)[1,1'-BIPHENYL]-3-CARBOXYLIC ACID synthesis
- Product Name:4'-(BENZYLOXY)[1,1'-BIPHENYL]-3-CARBOXYLIC ACID
- CAS Number:167627-37-4
- Molecular formula:C20H16O3
- Molecular Weight:304.34
121629-21-8
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Yield:167627-37-4 77%
Reaction Conditions:
with potassium carbonate in acetone; for 8 h;Reflux;
Steps:
4'-(Benzyloxy)-1,1'-biphenyl-3-carboxylic acid (1b)
To a mixture of acid 20 (1.1 g; 5.1 mmol) and potassium carbonate (1.08 g; 7.8 mmol) in acetone (70 mL), benzyl bromide (1.86 g; 10.8 mmol) was added and the reaction mixture was stirred and heated to boiling for 8 h. After cooling to room temperature, the mixture was diluted with water (60 mL) and extracted with chloroform (3 × 50 mL) and the solvent was evaporated. The residue was diluted with ethanol (50 mL) and a solution of sodium hydroxide (8.0 g; 0.2 mol) in water (12 mL) was added. The mixture was stirred at room temperature for 3 h, cooled to 0 °C and acidified with 15% aq. HCl to pH ~2. The precipitate was filtered off, washed with water (2 × 15 mL) and crystallized from toluene. 1.2 g (77%) of acid 1b was isolated, m. p. 221-223 °C. 1H NMR (acetone-d6): 5.20 (s, 2 H, OCH2), 7.16 (d, 2 H, J = 8.8, H-3, H-5), 7.40 (m, 3 H), 7.52 (m, 2 H), 7.57 (t, 1 H, H-5), 7.67 (d, 2 H, J = 8.8, H-2, H-6), 7.88 (d, 1 H, J = 8.2, H-6), 7.99 (d, 1 H, J = 7.6, H-4), 8.26 (s, 1 H, H-2). Elemental analysis: for C20H16O3 (304.35): calculated C 78.93, H 5.30; found C 78.78, H 5.15%.
References:
Kovarova, Anna;Svetlik, Svatopluk;Kozmik, Vaclav;Svoboda, Jiri;Novotna, Vladimira;Pociecha, Damian;Gorecka, Ewa;Podoliak, Natalia [Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 794 - 807] Location in patent:supporting information
146631-00-7
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167627-37-4
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