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Chemical Structure| 14615-72-6
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Product Details of [ 14615-72-6 ]

CAS No. :14615-72-6 MDL No. :MFCD00075777
Formula : C21H18O3 Boiling Point : -
Linear Structure Formula :- InChI Key :CHUAMRVJSRBRHT-UHFFFAOYSA-N
M.W : 318.37 Pubchem ID :561351
Synonyms :

Safety of [ 14615-72-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
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Application In Synthesis of [ 14615-72-6 ]

* 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.

  • Upstream synthesis route of [ 14615-72-6 ]
  • Downstream synthetic route of [ 14615-72-6 ]

[ 14615-72-6 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 24131-31-5 ]
  • [ 14615-72-6 ]
YieldReaction ConditionsOperation in experiment
93% With sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1 h; To a solution of 3,5-bis(benzyloxy)benzyl alcohol [2] (9.9 g, 31.0 mmol) in CH2Cl2 (140mL) was added DMSO (22 mL, 0.31 mol) and diisopropylethylamine (26.92 mL, 0.154mol). The mixture was cooled to 0 °C and SO3•pyridine (14.76 g, 92.73 mmol) added. The reaction stirred at 0 °C for one hour, after which it was quenched with saturated aqueous Na2S2O3 (310 mL). The solution was extracted with ethyl acetate (3 x 200 mL)and the organic layers combined and dried over MgSO4. Evaporation of the solvent afforded an oil which was purified by silica gel column chromatography in CH2Cl2 to give 9.2 g (93percent) of the desired product. The spectra was similar to data reported previously [3].
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 25, p. 9367 - 9374
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2950 - 2955
[3] Chemistry - A European Journal, 2009, vol. 15, # 10, p. 2278 - 2288
[4] ChemCatChem, 2017, vol. 9, # 20, p. 3880 - 3887
[5] ACS Catalysis, 2018, vol. 8, # 4, p. 3030 - 3034
[6] Journal of Organic Chemistry, 1997, vol. 62, # 4, p. 908 - 915
[7] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 6, p. 1889 - 1890
[8] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 2320 - 2327
[9] Journal of Medicinal Chemistry, 1985, vol. 28, # 1, p. 12 - 17
[10] Synthetic Communications, 2002, vol. 32, # 20, p. 3149 - 3158
[11] Journal of Medicinal Chemistry, 1997, vol. 40, # 8, p. 1186 - 1194
[12] Helvetica Chimica Acta, 1980, vol. 63, # 8, p. 2508 - 2514
[13] Chemistry - A European Journal, 2002, vol. 8, # 2, p. 408 - 432
[14] Russian Chemical Bulletin, 2004, vol. 53, # 4, p. 830 - 833
[15] Journal of the American Chemical Society, 1997, vol. 119, # 2, p. 283 - 291
[16] Journal of Heterocyclic Chemistry, 1973, vol. 10, p. 649 - 654
[17] Tetrahedron Letters, 1988, vol. 29, # 19, p. 2347 - 2348
[18] Synthetic Communications, 1998, vol. 28, # 6, p. 1097 - 1102
[19] Journal of the American Chemical Society, 2004, vol. 126, # 32, p. 9882 - 9883
[20] Journal of the American Chemical Society, 2006, vol. 128, # 10, p. 3324 - 3334
[21] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 1941 - 1944
[22] Synlett, 2008, # 12, p. 1801 - 1804
  • 2
  • [ 26153-38-8 ]
  • [ 100-39-0 ]
  • [ 14615-72-6 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In acetone at 0 - 40℃; for 12 h; Inert atmosphere General procedure: To the stirred solution of phenolic aldehyde (2.00 mmol) in anhydrous acetone (10 mL) was added K2CO3 (3.00 mmol, 1.5 eq.) In a nitrogen atmosphere0 And cooled.Benzyl bromide (2.4 mmol, 1.2 eq.) Was slowly added,The mixture temperature was raised to 40 ,Stir for 12 hours.After completion of the reaction, the reaction mixture was cooled to room temperature,Filter through a Celite pad and concentrate in vacuo.The crude compound was purified by column chromatography (EtOAc / Hexane = 1/3) to give the pure aromatic aldehyde in which the benzyl group was protected [note: two equivalents of K2CO3 were used in the synthesis of compound 18, 2.4 equivalents of benzyl bromide and 4.0 equivalents of K2CO3 was used for the synthesis of Compound 19).
82% With potassium carbonate; potassium iodide In acetone at 20℃; for 4 h; Inert atmosphere A stirred suspension of 3,5-dihydroxybenzaldehyde (690mg, 5mmol), potassium carbonate (3.46g, 25mmol) and potassium iodide (166.0mg, 1mmol) in acetone (15mL) was treated dropwise with benzyl bromide (1.18mL, 10mmol) and stirring continued for 4h at room temperature. The resulting suspension was concentrated under reduced pressure and the crude mass subjected to flash column chromatography (silica, 4:1 v/v hexane/ethyl acetate) and concentration of the relevant fractions (Rf=0.58 in 4:1 v/v hexane/ethyl acetate) afforded the title compound as a white powder (1.3g, 82percent) m.p. 80–81°C. (0031) 1H NMR (DMSO-d6, 500MHz): δ 9.91 (s, 1H), 7.48–7.44 (m, 4H), 7.43–7.38 (m, 4H), 7.37–7.32 (m, 2H), 7.17 (d, J=2.3Hz, 2H), 7.01 (t, J=2.3Hz, 1H), 5.17 (s, 4H) ppm. 13C NMR (DMSO-d6, 126MHz): δ 192.6, 159.9, 138.3, 136.6, 128.4, 127.9, 127.7, 108.2, 108.1, 69.6ppm. IR (diamond cell, neat) νmax: 1686, 1591, 1447, 1381, 1349, 1296, 1170, 1048, 829, 739, 719, 694, 675, 629cm−1. LRMS (+ESI) m/z: 319 [(M+H)+, 100percent]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5438 - 5443
[2] Patent: KR2018/16809, 2018, A, . Location in patent: Paragraph 0104; 0111-0113; 0116; 0124; 0125
[3] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 730 - 740
[4] Tetrahedron, 1994, vol. 50, # 38, p. 11097 - 11112
[5] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 5, p. 643 - 648
  • 3
  • [ 2150-44-9 ]
  • [ 14615-72-6 ]
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 10, p. 3324 - 3334
[2] Russian Chemical Bulletin, 2004, vol. 53, # 4, p. 830 - 833
[3] Journal of the American Chemical Society, 2004, vol. 126, # 32, p. 9882 - 9883
[4] Synthetic Communications, 2002, vol. 32, # 20, p. 3149 - 3158
[5] Journal of the American Chemical Society, 1997, vol. 119, # 2, p. 283 - 291
[6] Journal of Organic Chemistry, 1997, vol. 62, # 4, p. 908 - 915
[7] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2950 - 2955
[8] Helvetica Chimica Acta, 1980, vol. 63, # 8, p. 2508 - 2514
  • 4
  • [ 58605-10-0 ]
  • [ 14615-72-6 ]
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 10, p. 3324 - 3334
[2] Russian Chemical Bulletin, 2004, vol. 53, # 4, p. 830 - 833
[3] Journal of the American Chemical Society, 2004, vol. 126, # 32, p. 9882 - 9883
[4] Synthetic Communications, 2002, vol. 32, # 20, p. 3149 - 3158
[5] Journal of the American Chemical Society, 1997, vol. 119, # 2, p. 283 - 291
[6] Journal of Organic Chemistry, 1997, vol. 62, # 4, p. 908 - 915
[7] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2950 - 2955
[8] Helvetica Chimica Acta, 1980, vol. 63, # 8, p. 2508 - 2514
[9] Tetrahedron Letters, 1988, vol. 29, # 19, p. 2347 - 2348
  • 5
  • [ 99-10-5 ]
  • [ 14615-72-6 ]
Reference: [1] Russian Chemical Bulletin, 2004, vol. 53, # 4, p. 830 - 833
[2] Synthetic Communications, 2002, vol. 32, # 20, p. 3149 - 3158
[3] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 6, p. 1889 - 1890
[4] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 1941 - 1944
[5] Journal of Heterocyclic Chemistry, 1973, vol. 10, p. 649 - 654
  • 6
  • [ 29654-55-5 ]
  • [ 14615-72-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 8, p. 1186 - 1194
  • 7
  • [ 100-39-0 ]
  • [ 14615-72-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2950 - 2955
  • 8
  • [ 50513-72-9 ]
  • [ 14615-72-6 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 6, p. 1889 - 1890
[2] Journal of Heterocyclic Chemistry, 1973, vol. 10, p. 649 - 654
  • 9
  • [ 100-44-7 ]
  • [ 14615-72-6 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 1941 - 1944
  • 10
  • [ 85565-94-2 ]
  • [ 14615-72-6 ]
  • [ 85565-92-0 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 1941 - 1944
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