4-(2-CHLORO-PHENOXYMETHYL)-BENZOIC ACID synthesis
- Product Name:4-(2-CHLORO-PHENOXYMETHYL)-BENZOIC ACID
- CAS Number:149288-38-0
- Molecular formula:C14H11ClO3
- Molecular Weight:262.69
406470-63-1
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149288-38-0
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Yield:149288-38-0 95%
Reaction Conditions:
with hydrogenchloride;sodium hydroxide in tetrahydrofuran;methanol; for 3 h;Reflux;
Steps:
2 Step 2
To a solution of 54 (2.57?g, 9.78?mmol) in MeOH (20?ml) and THF (6?ml) was added 4?N NaOH (3.8?ml, 15?mmol) at room temperature.
The reaction mixture was heated to reflux for 3?h. After cooling to 0?°C, water, followed by 2?N HCl, was added portion-wise and the reaction mixture allowed to stir at room temperature.
The slurry was filtered and the filter cake washed with water, followed by drying in a vacuum to afford 4-((2-chlorophenoxy)methyl)benzoic acid (55; 2.43?g, 95%) as a white solid. 1H NMR (DMSO-d6) δ: 5.31 (s, 2H), 6.98 (td, J?=?7.5, 1.2?Hz, 1H), 7.22 (dd, J?=?8.3, 1.2?Hz, 1H), 7.28-7.32 (m, 1H), 7.46 (dd, J?=?7.9, 1.6?Hz, 1H), 7.59 (d, J?=?8.3?Hz, 2H), 7.98 (d, J?=?8.3?Hz, 2H), 12.99 (br s, 1H).
References:
Iida, Tetsuya;Ubukata, Minoru;Mitani, Ikuo;Nakagawa, Yuichi;Maeda, Katsuya;Imai, Hiroto;Ogoshi, Yosuke;Hotta, Takahiro;Sakata, Shohei;Sano, Ryuhei;Morinaga, Hisayo;Negoro, Tamotsu;Oshida, Shinichi;Tanaka, Masahiro;Inaba, Takashi [European Journal of Medicinal Chemistry,2018,vol. 158,p. 832 - 852]
95-57-8
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149288-38-0
14 suppliers
$617.00/1g
2417-72-3
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149288-38-0
14 suppliers
$617.00/1g