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Chemical Structure| 156276-21-0

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Product Details of [ 156276-21-0 ]

CAS No. :156276-21-0
Formula : C9H9ClO3
M.W : 200.62
SMILES Code : O=C(OC)C(C1=CC=CC=C1Cl)O
MDL No. :MFCD09833003
InChI Key :ZMPGBVQQIQSQED-UHFFFAOYSA-N
Pubchem ID :11321601

Safety of [ 156276-21-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 156276-21-0 ]

* 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.

  • Downstream synthetic route of [ 156276-21-0 ]

[ 156276-21-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 10421-85-9 ]
  • [ 156276-21-0 ]
YieldReaction ConditionsOperation in experiment
97% With sulfuric acid; at 60℃; General procedure: A few drops of conc. H2SO4 were added to a stirred solution of mandelic acid 6a (4.56 g, 29 mmol) in methanol (50 ml). The reaction was refluxed for 3 hours, after which the solvent was removed and the residue dissolved in ethyl acetate (25 ml). The product was washed with a 10% aqueous K2CO3 solution (2 x 50 ml) and then with brine (2 x 50 ml). The organic layer was dried (MgSO4) and reduced to give the title compound as a white crystalline solid,
With hydrogenchloride; In water; at 75℃; for 3.0h; Example 1. Preparing of racemic alkyl 2-chloromandelate[30][31] 2g of racemic <strong>[10421-85-9]2-chloromandelic acid</strong> was added to 40ml of methanol and 35 % HCl solution. The reaction was carried out at 75 0C for 3 hours. The reaction mixture was neutralized and racemic methyl 2-chloromandelate was gained by solvent extraction and distillation under reduced pressure. Racemic ethyl 2-chloromandelate and butyl <n="5"/>2-chloromandelate were synthesized using ethanol or buthanol, respectively instead of methanol. And the products were confirmed by nuclear magnetic resonance(Burker, Model DRS300).[32] Methyl 2-chloromandelate [33] 1H-NMR(CDCl , 300MHz) delta(ppm) = 3.76(s, 3H), 5.57(s, IH), 7.27(m, 2H), 7.39(m, 2H)[34] Ethyl 2-chloromandelate [35] 1H-NMR(CDCl , 300MHz) delta(ppm) = 1.21(t, 3H), 4.21(m, 2H), 5.54(s, IH), 7.27(m, 2H), 7.38(m, 2H)[36] Butyl 2-chloromandelate [37] 1H-NMR(CDCl , 300MHz) delta(ppm) = 0.83(t, 3H), 1.23(m, 2H), 1.54(m, 2H), 4.16(t, 2H), 5.56(s, IH), 7.25(m, 2H), 7.38(m, 2H)
With sulfuric acid; magnesium sulfate;Reflux; To a stirring solution of 1000 g racemic o-chloromandelic acid dissolved in 1 L methanol were added 120 g MgSO4 and 10 ml H2SO4. The mixture was refluxed with agitation until o-chloromandelic acid was completely consumed (as monitored by TLC). After cooled to room temperature, MgSO4, and methanol were removed by filtration and rotary evaporation. Then the mixture was neutralized by saturated Na2CO3 solution and dried over anhydrous Na2SO4 to give racemic CMM. To a stirring solution of 800 g CMM dissolved in 2 L CH2Cl2 and pre-cooled at 0-10oC was added Jones reagent which was prepared by adding grinded Cr2O3 powder (530 g) into stirring concentrated H2SO4 (460 ml) followed by diluting with water to 2 L. The progress of the reaction was monitored by TLC analysis till the reaction was completed. The organic layer was separated and washed with saturated Na2CO3 solution, dried over anhydrous Na2SO4 and evaporated to give CBFM as pale yellow oil with an isolated yield of 82%. 1H NMR (CDCl3, 400 MHz): delta/ppm: 3.96 (3H, s, OCH3), 7.41-7.46 (2H, m, Ar-H), 7.51-7.54 (1H, m, Ar-H), 7.75-7.78 (1H, m, Ar-H); 13C NMR (CDCl3, 100 MHz): delta/ppm: 53.9, 127.9, 131.2, 132.2, 133.9, 134.5, 135.0, 164.1, 186.9.
With toluene-4-sulfonic acid; In toluene; for 2.0h;Reflux; General procedure: A mixture of mandelic acid(12 mmol), alcohol (1.5 eq) , TsOH (500 mg) and toluene(20mL) wasrefluxed for 2 h. The resultant mixture was diluted with NaHCO3(sat.aq.)(3X10mL) and water( 2X10mL) and dried over Na2SO4.Flash chromatography on silica gel (eluent: ethyl acetate/petroleum ether =6:1) gave the correspondingracemic mandelate ester.
With sulfuric acid; at 80℃; for 3.0h; Example 3. Preparing racemic 2-chloro-2-(2-chloro phenyl)acetic acid alkyl ester(ld, Ie, If); [52][53] 3g of <strong>[10421-85-9]2-chloromandelic acid</strong> was dissolved into 40 ml of methanol and after adding88 D of HSO , the mixture was heated and stirred at 80 0C for 3 hours. After removing solvent, water and ethyl acetate were added, then NaOH was added for neutralization. The product was extracted and distilled under reduced pressure. 2.1 ml of sulfonyl chloride was added to the previously produced substance and after 12 hours of stirring at 65 0C, solvent was removed. 2-chloro-2-(2-chloro phenyl)acetic acid methyl ester was prepared by adding water and ethyl acetate and washing 3 times. Furthermore, by using ethanol and butanol instead of methanol, 2-chloro-2-(2-chloro phenyl)acetic acid ethyl ester and 2-chloro-2-(2-chloro phenyl)acetic acid butyl ester were prepared respectively.[54] 2-chloro-2-(2-chloro phenyl)acetic acid methyl ester(ld):[55] 1H-NMRQOOMHz) delta(ppm) = 3.79(s, IH), 5.88(s, IH), 7.31(m,2H), 7.40(m,lH),7.63(m, IH)[56][57] 2-chloro-2-(2-chloro phenyl)acetic acid ethyl ester(le):[58] 1H-NMRQOOMHz) delta(ppm) = 1.26(t, 3H, J=14.1 Hz), 4.25(m, IH), 5.86(s, IH),7.32(m, 2H), 7.40(m, IH), 7.63(m, IH)[59][60] 2-chloro-2-(2-chloro phenyl)aceetic acid butyl ester(lf) :[61] 1H-NMRQOOMHz) delta(ppm) = O.88(t, 3H, J=14.4 Hz), 1.3 l(m, 2H), 1.61(m, 2H),4.19(t, 2H, J=13.5 Hz), 5.87(s, IH), 7.32(m, 2H), 7.40(m, IH), 7.63(m, IH)

  • 2
  • [ 10421-85-9 ]
  • [ 18107-18-1 ]
  • [ 156276-21-0 ]
 

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