Methyl 2-(2-chlorophenyl)-2-hydroxyacetate synthesis

8synthesis methods

Product Name:Methyl 2-(2-chlorophenyl)-2-hydroxyacetate
CAS Number:156276-21-0
Molecular formula:C9H9ClO3
Molecular Weight:200.62

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Methyl 2-(2-chlorophenyl)-2-hydroxyacetate

156276-21-0
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Yield:156276-21-0 95%

Reaction Conditions:

with methanol;benzaldehyde;1,3-bis(mesityl)imidazolium chloride;triethylamine at 25; for 5 h;Inert atmosphere;regioselective reaction;Cannizzaro type reaction;

Steps:

10 Typical procedure for NHC(A)-mediated reduction of α-keto ester 2:

General procedure: To a mixture of imidazolium salt A (48 mg, 0.14 mmol) and distilled benzaldehyde (300 mg, 2.83 mmol) in MeOH (9.0 mL) was added triethylamine (21.5 mg, 0.21 mmol) followed by methyl 2-(2-chlorophenyl)-2-oxoacetate (842 mg, 4.24 mmol) under nitrogen atmosphere. The mixture was then stirred at 25 °C for 5 h until benzaldehyde was consumed (monitored by TLC). After completion of the reaction the mixture was concentrated under vacuum and the residue was purified by flash chromatography on silica gel (230-400 mesh) using 10-15% EtOAc-hexane; spectral data of 4a: IR (film) 3467, 2954, 1741, 1222, 756 cm^-1; ¹H NMR (400 MHz, DMSO-d₆): δ 7.43-7.53 (2H, m, CH_arom), 7.32-7.39 (2H, m, CH_arom), 6.36 (1H, d, J = 5.6 Hz, OH), 5.44 (1H, d, J = 6.0 Hz, C₆H₄CHOH); 3.62 (3H, s, OCH₃); ¹³C NMR (100 MHz, CDCl₃): δ 52.8, 70.1, 126.9, 128.6, 129.5, 129.6, 133.2, 135.9, 173.3; mass (ES) m/z 223 (M+Na)⁺; HRMS calculated for C₉H₁₀O₃Cl [M+H]⁺ 201.0318. Found 201.0323. Compound 4f: IR (film) 3460, 2954, 1741, 1215, 772 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ 7.26-7.43 (4H, m, CH_arom), 5.15 (1H, d, J = 5.6 Hz, C₆H₄CHOH), 3.77 (3H, s, OCH₃), 3.55 (1H, d, J = 5.6 Hz, OH); ¹³C NMR (50 MHz, CDCl₃): δ 53.1, 72.2, 124.7, 126.6, 128.5, 129.7, 134.4, 140.0, 173.4; mass (ES) m/z 223 (M+Na)⁺; HRMS calculated for C₉H₁₀O₃Cl [M+H]⁺ 201.0318. Found 201.0327.

References:

Sreenivasulu;Arun Kumar;Sateesh Reddy;Siva Kumar;Rajender Kumar;Chandrasekhar;Pal, Manojit [Tetrahedron Letters,2011,vol. 52,# 6,p. 727 - 732] Location in patent:supporting information; experimental part