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Chemical Structure| 14714-50-2
Chemical Structure| 14714-50-2
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Product Details of [ 14714-50-2 ]

CAS No. :14714-50-2 MDL No. :MFCD00128130
Formula : C8H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :WMWRBGOAZXDIDN-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :10582824
Synonyms :

Safety of [ 14714-50-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14714-50-2 ]

* 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.

  • Upstream synthesis route of [ 14714-50-2 ]
  • Downstream synthetic route of [ 14714-50-2 ]

[ 14714-50-2 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 773837-37-9 ]
  • [ 90-01-7 ]
  • [ 14714-50-2 ]
YieldReaction ConditionsOperation in experiment
84% at 120℃; for 4 h; In a 2 L round bottom flask reactor, 2-hydroxymethylphenol (100 g, 806 mmol), sodium cyanide (43.4 g, 886 mmol) and dimethylformamide (1000 mL) were charged and stirred at 120 ° C for 4 hours. After the reaction was over, extraction was performed with water and ethyl acetate. After concentration, the separation was carried out by column chromatography to obtain Intermediate 5-a (90 g, 84percent).
84% at 120℃; for 4 h; A 2 L reactor was charged with 2-hydroxymethylphenol (100 g, 806 mmol),Sodium cyanide (43.4 g, 886 mmol),Add 1000 mL of dimethylformamide and stir at 120 ° C for 4 hours. After completion of the reaction, the reaction mixture is extracted with water and ethyl acetate.Concentrated and then separated by column chromatography to obtain Intermediate 5-a (90 g, 84percent).
81% at 120℃; for 4 h; 2L reactor to the second-hydroxymethyl-phenol 100 g (806 mmol), sodium cyanide 43.4 g (886 mmol), 1000 mL of dimethylformamide into a 120 °C 4 hours dongan stirring. After the reaction and extracted with water and ethyl acetate. It was concentrated and separated by column chromatography to obtain 90 g. (Yield 81percent)
80% at 100℃; for 12 h; Inert atmosphere A solution of 2-hydroxymethyl phenol (3.9 g, 30 mmol) in DMF (30 mL) was added to sodium cyanide (2.9 g, 60 mmol), andthe resulting mixture was stirred at 100 °C for 12 h. After the resulting solution was cooled to room temperature, it was poured into 10percent HCl aqueous solution (30 mL), and extracted with Et2O (30 mL×3). The combined organic layer was dried over MgSO4, and the organic solvent was removed under reduced pressure. The residue was filtered through a short silica gel pad followed by recrystallization from hexane / CHCl3 to furnish 2-(cyanomethyl)phenol 3a (3.2 g, 24 mmol, 80percent yield) as a pale yellow solid.

Reference: [1] Patent: CN107459523, 2017, A, . Location in patent: Paragraph 0285; 0286; 0287; 0288; 0289
[2] Patent: KR2018/14985, 2018, A, . Location in patent: Paragraph 0550-0556
[3] Patent: KR2016/26661, 2016, A, . Location in patent: Paragraph 0455-0461
[4] Tetrahedron, 2015, vol. 71, # 26-27, p. 4432 - 4437
  • 2
  • [ 1058648-87-5 ]
  • [ 10442-39-4 ]
  • [ 14714-50-2 ]
YieldReaction ConditionsOperation in experiment
84% at 135 - 140℃; for 0.075 h; Microwave irradiation General procedure: A mixture of MOM–ethers (1 mmol) [Bu4N][X](2 mmol) was added to [Hmim][NO3] (0.4 mmol) (and exposed to MWirradiation (All reactions were carried out at 135-140 oC with 170 Wapplied power). After completion of the reactions (monitored by TLC, eluent:n–hexane/ethyl acetate, 5:1), the mixture was extracted with Et2O(3×10 mL). The organic phase was dried over anhydrous Na2SO4and rotary evaporation afforded a residue, which was then passed through ashort pad of neutral alumina (n–hexane/ethyl acetate, 5:1, 75 mL) to obtain thehighly pure products. The spectral data were inaccordance with those reported in the literature:
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 32, p. 4424 - 4426
[2] Tetrahedron Letters, 2010, vol. 51, # 25, p. 3274 - 3276
  • 3
  • [ 538342-16-4 ]
  • [ 14714-50-2 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 18, p. 5282 - 5283
  • 4
  • [ 90-01-7 ]
  • [ 14714-50-2 ]
YieldReaction ConditionsOperation in experiment
47% at 130℃; for 8 h; 2-Hydroxybenzylalcohol (5.0 g, 40.3 mmol) and potassium cyanide (3.0 g, 61.2 mmol) were dissolved in DMF (80 mL) and the solution was heated to 130 °C with stirring. After 8 h, the mixture was quenched with saturated aqueous NH4Cl (200 mL), which was extracted with EtOAc (100 mL.x.3). The combined organic layer was washed with saturated aqueous NH4Cl (50 mL.x.3), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography (40percent EtOAc/n-hexane) to obtain 2-hydroxybenzyl cyanide (2.5 g, 47percent) as brown solid: mp 113-114 °C (116-118 °C in literature18); 1H NMR (400 MHz, CDCl3) δ 3.73 (s, 2H), 5.54 (s, 1H, OH), 6.80 (dd, J=8.0, 0.8 Hz, 1H), 6.95 (td, J=7.2, 0.8 Hz, 1H), 7.20 (td, J=8.0, 1.6 Hz, 1H), 7.34 (dd, J=7.2, 1.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 18.5, 115.3, 116.8, 118.0, 121.2, 129.48, 129.57, 153.1; MS (EI) m/z 133 (M+, 100). Registry No.: 14714-50-2.
Reference: [1] Tetrahedron, 2012, vol. 68, # 21, p. 3942 - 3947
  • 5
  • [ 325141-71-7 ]
  • [ 14714-50-2 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 32, p. 7291 - 7294
  • 6
  • [ 90-01-7 ]
  • [ 143-33-9 ]
  • [ 14714-50-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 6, p. 1989 - 2007
[2] Patent: WO2007/53082, 2007, A1, . Location in patent: Page/Page column 86
  • 7
  • [ 7035-03-2 ]
  • [ 14714-50-2 ]
Reference: [1] Heterocycles, 2011, vol. 83, # 6, p. 1355 - 1361
[2] Helvetica Chimica Acta, 2013, vol. 96, # 2, p. 296 - 308
  • 8
  • [ 40053-98-3 ]
  • [ 14714-50-2 ]
Reference: [1] Patent: US4069340, 1978, A,
[2] Patent: US3983178, 1976, A,
  • 9
  • [ 1058648-91-1 ]
  • [ 10442-39-4 ]
  • [ 14714-50-2 ]
Reference: [1] Comptes Rendus Chimie, 2010, vol. 13, # 12, p. 1468 - 1473
[2] Tetrahedron Letters, 2010, vol. 51, # 25, p. 3274 - 3276
  • 10
  • [ 40149-56-2 ]
  • [ 14714-50-2 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 18, p. 5282 - 5283
  • 11
  • [ 90-01-7 ]
  • [ 14714-50-2 ]
Reference: [1] Patent: US3983160, 1976, A,
  • 12
  • [ 10442-39-4 ]
  • [ 942588-45-6 ]
  • [ 14714-50-2 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 10, p. 3435 - 3441
  • 13
  • [ 346433-42-9 ]
  • [ 14714-50-2 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 10, p. 3435 - 3441
  • 14
  • [ 610-66-2 ]
  • [ 14714-50-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 10, p. 3424 - 3445
  • 15
  • [ 69-72-7 ]
  • [ 14714-50-2 ]
Reference: [1] Tetrahedron, 2015, vol. 71, # 26-27, p. 4432 - 4437
  • 16
  • [ 2973-50-4 ]
  • [ 14714-50-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 10, p. 3424 - 3445
  • 17
  • [ 92497-64-8 ]
  • [ 14714-50-2 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 3512 Anm.
  • 18
  • [ 704-65-4 ]
  • [ 143-33-9 ]
  • [ 14714-50-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1979, vol. II, # 5-6, p. 241 - 248
  • 19
  • [ 108-24-7 ]
  • [ 14714-50-2 ]
Reference: [1] Journal of the Chemical Society, 1933, p. 489,493
[2] Chemische Berichte, 1947, vol. 80, p. 469,472
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