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CAS No. : | 51019-44-4 | MDL No. : | |
Formula : | C10H9ClO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 212.63 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Stage #1: (S)-Mandelic acid; acetyl chloride for 2h; Stage #2: With thionyl chloride at 75℃; for 3h; | (R)- and (S)-2-chloro-2-oxo-1-phenylethylacetate In a round bottom flask (R)- or (S)-mandelic acid (8.88 g, 58 mmol) were dissolved in acetyl chloride (74.6 g, 950 mmol, 68 mL, 16.3 eq.). The solution was stirred for 2 h and the excess of acetyl chloride was evaporated. The intermediate was dried overnight in vacuum and used without further purification. Subsequently, thionyl chloride (65.5 g, 55 mmol, 40 mL, 9.5 eq.) was added and the solution was heated for 3 h at 75 °C. The excess of thionyl chloride was removed in vacuum at 60 °C. Yield: for (R) 11.81 g 95%, for (S) 11.90 g 96%. 1H-NMR (CDCl3, 500 MHz): δ (in ppm): 2.21 (s, 3 H, 4-H), 6.07 (s, 1 H, 2-H), 7.43-7.50 (m, 5 H, 6-H, 7-H, 8-H). 13C-NMR (DMSO-d6, 125 MHz): δ (in ppm): 20.43 (CH3, C-4), 80.85 (CH, C-2), 128.39 (CH, C-7), 129.19 (CH, C-6), 130.23 (CH, C-8), 130.77 (Cq, C-5), 169.92 (Cq, C-3), 170.75 (Cq, C-1). |
Stage #1: (S)-Mandelic acid; acetyl chloride at 20℃; Schlenk technique; Inert atmosphere; Stage #2: With thionyl chloride In N,N-dimethyl-formamide at 20℃; Schlenk technique; Inert atmosphere; |