ChemicalBook CAS DataBase List 2-[(4-chlorophenyl)methyl]benzoic acid

2-[(4-chlorophenyl)methyl]benzoic acid synthesis

6synthesis methods

Product Name:2-[(4-chlorophenyl)methyl]benzoic acid
CAS Number:4889-70-7
Molecular formula:C14H11ClO2
Molecular Weight:246.69

85-56-3 Synthesis

85-56-3
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$5.00/10g

4889-70-7
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$662.15/1G

Yield:4889-70-7 95%

Reaction Conditions:

with copper(ll) sulfate pentahydrate;ammonia;zinc in water at 130; for 48 h;

Steps:

Preparation of 1c

2-(4-chlorobenzoyl) benzoic acid (1.6 g, 6 mmol) was added to 80 ml ammonia (28% aq), followed by CuSO₄·5H₂O (0.6 g, 2.4 mmol) and Zn (4.7 g, 72 mmol). The mixture was refluxed 48 h and added 15 mL ammonia (28% aq) per 6 h. After that the mixture was cooled to r.t. and filtrated. The filtrate was adjusted to pH = 1 with concentrated hydrochloric acid and extracted by ethyl acetate. Then solvent was evaporated and the crude residue was purified by column chromatography (petroleum ether/EtOAc = 5/1) to afford 2-(4-chlorobenzyl) benzoic acid (1c) 1.41 g as a white solid (yield = 95%).² IR (KBr): 1676.35, 1574.02, 1491.77, 1406.53, 1310.97,1274.29, 1254.78, 835.03, 738.41.¹H NMR (400 MHz, CDCl₃) δ = 8.10 (dd, 1H, ArH), 7.52 (td,1H, ArH), 7.36 (t, 1H, ArH), 7.25 (m, 3H, ArH), 7.11 (d, 2H, ArH), 4.44 (s, 2H, CH2). ¹³C NMR(100 MHz, CDCl₃): δ = 172.04, 142.88, 139.24, 133.14, 131.87, 131.78, 130.30, 128.45, 128.25,126.66, 39.06.

References:

Wang, Yabai;Yang, Shiwei;Bian, Guangling;Song, Ling [Synthesis,2017,vol. 49,# 8,p. 1884 - 1888] Location in patent:supporting information