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CAS No. : | 1129-46-0 | MDL No. : | MFCD04038077 |
Formula : | C9H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SXERGJJQSKIUIC-SSDOTTSWSA-N |
M.W : | 166.17 | Pubchem ID : | 643326 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
99% | With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 6h; | Oxalyl chloride (1.09 mL, 12.5 mmol) was added to a solution of acid (R)-5 (0.83 g, 5 mmol) and DMF (5 μL) in CH2Cl2 (20 mL). The reaction mixture was stirred at room temperature for 6 h, and then evaporated to dryness under reduced pressure. The residue was dried over P2O5 in vacuo to afford 0.92 g (99%) of compound (R)-2a as a yellowish oil, which had an unpleasant odor. Anal. Calcd for C9H9ClO2: C, 58.55; H, 4.91. Found: C, 58.78; H, 5.07. 1H NMR spectrum was identical to that published for racemic chloride 2a. 5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium hydroxide; In ethanol; at 4 - 20℃; for 24h; | At first, 2 M NaOH (5.2 mL, 10.4 mmol) was added dropwise to a solution of compound (R)-4 (1.01 g, 5.2 mmol) in ethanol (20 mL) with stirring at 4 C. The reaction mixture was stirred at room temperature for 24 h, and then evaporated to dryness under reduced pressure. The residue was dissolved in water (40 mL), washed with ethyl ether (2 * 10 mL), acidified with 4 M HCl to pH 1-2 and extracted with ethyl ether (4 * 20 mL). The organic layers were washed with saturated aqueous NaCl (2 * 40 mL), dried over MgSO4, and evaporated to dryness under reduced pressure. The residue was recrystallized from hexane to yield 0.77 g (89%) of compound (R)-5 as a colorless solid, mp 86-88 C (hexane) (lit. 85-87 C, 12 83 C 13 ); [α]D20 = +16.2 (c 0.6, CHCl3) {lit. 13 [α]D20 = +19 (c 1.0, CHCl3)}. HPLC (Chiralpak AD, n-hexane-iPrOH-TFA 20:1:0.02): 95.6% ee. Anal. Calcd for C9H10O3: C, 65.05; H, 6.06. Found: C, 64.95; H, 6.24. 1H and 13C NMR spectra were identical to those published for (S)-5.14 |
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