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Product Details of [ 2111-75-3 ]

CAS No. :2111-75-3
Formula : C10H14O
M.W : 150.22
SMILES Code : O=CC1=CCC(C(C)=C)CC1
MDL No. :MFCD00062990

Safety of [ 2111-75-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H317-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis [ 2111-75-3 ]

* 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 [ 2111-75-3 ]

[ 2111-75-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 2111-75-3 ]
  • [ 536-59-4 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogen; sodium hydroxide In ethanol at 50℃; for 16 h; Autoclave; Inert atmosphere Example 13Hydrogenation Reaction of Perillaldehyde (S/C=500)Into a stainless steel autoclave equipped with a glass inner tube, [Cu(NO3)(PPh3)2] (11.7 mg, 0.018 mmol) and DPPB (7.7 mg, 0.018 mmol) were introduced. The inside of the autoclave was then replaced with nitrogen. To the autoclave, an ethanolic solution of sodium hydroxide (0.03 M) (6.0 mL, 0.18 mmol) and perillaldehyde (2.02 mL, 9 mmol) were added, and stirring was performed at a hydrogen pressure of 5 MPa at 50° C. for 16 hours. The hydrogen was released with great care, and the conversion was analyzed by GC (>99percent). The contents were concentrated, and then purified by silica gel chromatography. Thus, 1.26 g of the corresponding alcohol was obtained. obtained.
92% With hydrogen; sodium hydroxide In ethanol at 50℃; for 16 h; Autoclave; Inert atmosphere (Example 13) Hydrogenation Reaction of Perillaldehyde (S/C=500) Into a stainless steel autoclave equipped with a glass inner tube, [Cu(NO3)(PPh3)2] (11.7mg, 0.018 mmol) and DPPB (7.7 mg, 0.018 mmol) were introduced. The inside of the autoclave was then replaced with nitrogen. To the autoclave, an ethanolic solution of sodium hydroxide (0.03 M) (6.0 mL, 0.18 mmol) and perillaldehyde (2.02 mL, 9 mmol) were added, and stirring was performed at a hydrogen pressure of 5 MPa at 50°C for 16 hours. The hydrogen was released with great care, and the conversion was analyzed by GC (>99percent). The contents were concentrated, and then purified by silica gel chromatography. Thus, 1.26 g of the corresponding alcohol was obtained. Isolated yield: 92percent, 1d/2d = 52/1
35% With 1,1'-bis-(diphenylphosphino)ferrocene; silver(I) hexafluorophosphate; tripropylsilane; N-ethyl-N,N-diisopropylamine In water at 100℃; for 24 h; General procedure: Degassed CH2Cl2 (0.25 mL) was added to a microwave tube containing the ligand dppf (8.3 mg, 0.015 mmol) and AgPF6 (2.5 mg, 0.01 mmol) under argon. The resulting suspension was stirred at r.t., until a clear, colorless solution was obtained; then the solvent was removed under high vacuum. Benzaldehyde (1a; 20.3 μL, 0.2 mmol), tripropylsilane (2a;125 μL, 0.6 mmol), DIPEA (6.9 μL, 0.04 mmol), and H2O(0.5 mL) were subsequently added. The reaction mixture was stirred for 24 h at 100 °C, then cooled to r.t. and extracted with CH2Cl2 (3 × 10 mL). The combined organicphase was concentrated and purified by flash column chromatography on silica gel (hexane–EtOAc, 20:1) to give the desired product 3a as a colorless oil (19.5 mg, 90percent).
References: [1] Tetrahedron Letters, 1993, vol. 34, # 2, p. 257 - 260.
[2] Chemistry - A European Journal, 2017, vol. 23, # 35, p. 8473 - 8481.
[3] Synlett, 2009, # 8, p. 1295 - 1298.
[4] Patent: US2011/201819, 2011, A1, . Location in patent: Page/Page column 10.
[5] Patent: EP2377841, 2011, A1, . Location in patent: Page/Page column 13-14.
[6] Chemistry - A European Journal, 2013, vol. 19, # 17, p. 5255 - 5258.
[7] Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8809 - 8814.
[8] Tetrahedron, 1990, vol. 46, # 9, p. 3315 - 3320.
[9] Tetrahedron Letters, 1990, vol. 31, # 8, p. 1185 - 1186.
[10] Synlett, 2013, vol. 24, # 16, p. 2049 - 2056.
[11] Phytochemistry (Elsevier), 1986, vol. 25, # 12, p. 2769 - 2776.
[12] Patent: US2011/201820, 2011, A1, . Location in patent: Page/Page column 8.
[13] Patent: EP2374783, 2011, A1, . Location in patent: Page/Page column 11.
[14] Chemistry Letters, 2013, vol. 42, # 6, p. 660 - 662.
[15] Catalysis Science and Technology, 2015, vol. 5, # 6, p. 3108 - 3112.
[16] Organic Letters, 2018, vol. 20, # 16, p. 5040 - 5043.
  • 2
  • [ 2111-75-3 ]
  • [ 18479-64-6 ]
  • [ 536-59-4 ]
References: [1] Chemical Communications, 2013, vol. 49, # 63, p. 7034 - 7036.
[2] Patent: JP2015/48349, 2015, A, . Location in patent: Paragraph 0074-0076.
  • 3
  • [ 2111-75-3 ]
  • [ 536-59-4 ]
References: [1] RSC Advances, 2015, vol. 5, # 57, p. 46026 - 46030.
 

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