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Chemical Structure| 76448-73-2 Chemical Structure| 76448-73-2

Structure of 76448-73-2

Chemical Structure| 76448-73-2

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Product Details of [ 76448-73-2 ]

CAS No. :76448-73-2
Formula : C8H10O4
M.W : 170.16
SMILES Code : O=C(C1=CC=C(CO)O1)OCC

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Application In Synthesis of [ 76448-73-2 ]

* 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 [ 76448-73-2 ]

[ 76448-73-2 ] Synthesis Path-Downstream   1~3

  • 2
  • [ 64-17-5 ]
  • [ 17510-99-5 ]
  • [ 6338-41-6 ]
  • [ 76448-73-2 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In water; at 80℃; for 18h; In a separate experiment, 5 mL of an ethanol/water mixture (v/v, 9/1) containing 1.5 M of H2SO4 and 200 mM of purified DHG was placed in two vials. One vial was incubated with stirring at 80 C. and the other at 100 C. for 18 hours. HPLC analysis of the reactions confirmed the formation of HFCA at about 70% molar yield for the 80 C. reaction and about 55% yield for the reaction at 100 C. (and >95% conversion). The previous yield includes both HFCA free acid and the HFCA-ethyl ester (about 1/1 ratio in each reaction). The product identity and quantification was done by comparison with authentic standards by HPLC.
  • 3
  • [ 22860-23-7 ]
  • [ 64-17-5 ]
  • [ 6338-41-6 ]
  • 2,4-di-O-acetyl-D-erythro-hex-2-enono-1,5-lactone [ No CAS ]
  • 2-O-acetyl-D-erythro-hex-2-enono-1,5-lactone [ No CAS ]
  • [ 76448-73-2 ]
YieldReaction ConditionsOperation in experiment
17%; 26 mg; 56 mg; 34% With acetyl chloride; at 22℃; for 72h; A crude syrup of 1 (1.180 g) was dissolved in 10 mL Absolut EtOH and to the resulting mixture was added AcCI (58 pL, 0.2 eq) at 22 C. After 3 days, TLC analysis indicated full conversion of the starting material and the reaction mixture was concentrated, dissolved in acetone and concentrated on silica. This material was purified by column chromatography (1 : 51: 34: 6 acetone/toluene) to give the title compound 3 (240 mg, 34 %). *H NMR (500 MHz, CDCb) d 7.11 (d, J = 3.5 Hz, 1H, H3), 6.40 (d, J = 3.5 Hz, 1H, H2), 4.67 (s, 2H, H6), 4.35 (q, J = 7.1 Hz, 2H, HllEt), 2.24 (br s, 1H, H70H), 1.36 (t, J = 7.1 Hz, 3H, H12Et).13C NMR (126 MHz, CDCb) d 158.9 (Cl), 158.3 (C8C0), 144.5 (C4), 118.8 (C3), 109.5 (C2), 61.2 (CllEt), 57.7 (C6), 14.5 (C12Et). HRMS (ESP-TOF) m/z for C8HioNa04+(MNa+) calculated : 193.0471; found : 193.0478. Besides 3, the following was also isolated, 5-(hydroxymethyl)furan-2-carboxylic acid (98 mg, 17 %), 2, 4-di-0-acetyl-D-erythro-hex-2-enono-l, 5-lactone (26 mg) and 2-0-acetyl-D-erythro-hex-2-enono-l, 5-lactone (56 mg).
 

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