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Chemical Structure| 70918-53-5 Chemical Structure| 70918-53-5

Structure of 70918-53-5

Chemical Structure| 70918-53-5

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CAS No.: 70918-53-5

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Product Details of [ 70918-53-5 ]

CAS No. :70918-53-5
Formula : C9H8O4
M.W : 180.16
SMILES Code : O=C([C@@H]1OC2=CC=CC=C2OC1)O
MDL No. :MFCD00239407
InChI Key :HMBHAQMOBKLWRX-MRVPVSSYSA-N
Pubchem ID :687062

Safety of [ 70918-53-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 70918-53-5 ]

* 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 [ 70918-53-5 ]

[ 70918-53-5 ] Synthesis Path-Downstream   1~2

  • 1
  • 1,4-benzodioxane-2-carboxylic acid [ No CAS ]
  • [ 70918-54-6 ]
  • [ 70918-53-5 ]
  • 2
  • [ 3663-79-4 ]
  • [ 70918-54-6 ]
  • [ 70918-53-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: Racemic methyl 1,4-benzodioxan-2-carboxylate 17a (50 mg), aqueous phosphate buffer (2.5 mL, 0.1 M, pH. 7.1), n-butanol (500 μl), and wet whole cells of Arthrobacter sp. lipase (100 mg) were shaken (320 rpm) continuously at 25 ± 1 C. After a certain degree of conversion (～42%) as indicated by chiral high performance liquid chromatography (HPLC), the reaction was terminated by adding ethyl acetate and centrifuging the mixture at 10,000-15,000 g to remove the enzyme and the suspended particles. The clear solution was decanted and the centrifuged mass was extracted separately with ethyl acetate (3 × 25 mL). The organic layers were combined, washed with water, and treated with 2 M NaOH solution to give (S)-2,3-hydrobenzo[1,4]dioxane-2-carboxylic acid as its salt. The salt was neutralized with dilute HCl to give enantiomerically pure (S)-2,3-dihydrobenzo[1,4]dioxane-2-carboxylic acid (yield 42%). ee = 99%; mp = 102-103 C; [α]D25=-61.0 (c 1, CHCl3); Abs, config. (S); {lit.23b [α]25D=-63.8(c 1, CHCl3); ee = 99.0%; mp 97.5 C}; HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 20.78 and t2 = 22.87 min}. The organic layer was dried and evaporated under reduced pressure to furnish the optically active unhydrolyzed ester. ee = 73%; mp = 58-61 C; [α]D25=+46.4(c 1, CHCl3) [lit.23b [α]D25=57.0 (c 1, CHCl3), mp 78.1]; Abs. config. (R); HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 31.74 and t2 = 33.34 min}. The enantiomerically pure ester with ee = 99%; mp = 73-76 C; [α]25D=+55.4 (c 1, CHCl3); Abs. config. (R); {lit.23b [α]D25=+57.0 (c 1, CHCl3); ee = 99.4%; mp 78.5 C}, was obtained in the case of hydrolysis with diisopropylether as the co-solvent (Table 2, entry 13).
 

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