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CAS No. :37942-07-7 MDL No. :MFCD00191998
Formula : C15H22O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RRIQVLZDOZPJTH-UHFFFAOYSA-N
M.W :234.33 Pubchem ID :688023
Synonyms :

Safety of [ 37942-07-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 37942-07-7 ]

* 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 [ 37942-07-7 ]
  • Downstream synthetic route of [ 37942-07-7 ]

[ 37942-07-7 ] Synthesis Path-Upstream   1~8

  • 1
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  • [ 135616-40-9 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With sodium hydroxide In ethanol; water
Stage #2: for 1 h; Heating / reflux
(R,R)-N,N'-Bis(5-3-tert-butyl-salicylidene)-l,2-cyclohexanediamine was synthesized following a similar procedure described by Jacobsen E. N., Zhang W., Muci A. R., Ecker J. R., and Deng L. Highly Enantioselective Epoxidation Catalysts Derived from 1,2- Diaminocyclohexane, J. Am. Chem. Soc, 113, 7063-7064 (1991). To a 250 mL round bottom flask was added 2.0053 g (8.5573 mmol) of 3,5 -tert butyl-2-hydroxybenzaldehyde that was dissolved in 20 mL absolute ethanol. Concurrently, (R5R)- 1,2-diammoniumcyclohexane mono-(+)-tartrate salt {see Larrow J. F., Jacobsen E. N., Gao Y., Hong Y., Nie X., and Zepp C. M., A Practical Process for the Large-Scale Preparation of (R,R)-N,N'-Bis(3,5-Di-tert- butylsalicylidene)-l,2-Cyclohexanediaminomanganese (III) Chloride, a Highly Enantioselective Epoxidation Catalyst, J. Org. Chem., 59, 1939-1940 (1994); (1.1219 g, 4.2451 mmol) was dissolved in a basic (NaOH) 0.2 M aqueous/absolute ethanol solution (1 :2). This salt solution was added dropwise to the benzaldehyde solution and the mixture was refluxed under nitrogen for 1 hour. The reaction mixture was filtered using a 60 mL medium frit and washed with 95percent ethanol. The product was then extracted into methylene chloride. The frit was washed with additional methylene chloride until the solid was colorless. The solvent was removed under reduced pressure to yield 1.6843 gm (70percent) of a yellow solid. 1H NMR: (CDCl3, ppm) δ = 1.24 (s, 9H); 1.41 (s, 9H); 1.45 (m, IH); 1.65 - 1.8 (m, IH); 1.8 - 2.0 (m, 2H); 3.32 (m, IH); 6.98 (d, IH); 7.30 (d, IH); 8.30 (s, IH); 13.72 (s, IH).
Reference: [1] Organic Syntheses, 1998, vol. 75, p. 1 - 1
[2] Patent: WO2006/133354, 2006, A2, . Location in patent: Page/Page column 10
[3] Tetrahedron Asymmetry, 2001, vol. 12, # 2, p. 197 - 204
[4] Tetrahedron Letters, 2005, vol. 46, # 22, p. 3829 - 3830
[5] Applied Catalysis A: General, 2010, vol. 373, # 1-2, p. 57 - 65
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Reference: [1] Macromolecules, 2003, vol. 36, # 10, p. 3498 - 3504
[2] Macromolecules, 2004, vol. 37, # 20, p. 7469 - 7476
[3] Helvetica Chimica Acta, 2002, vol. 85, # 10, p. 3301 - 3312
[4] Tetrahedron, 2004, vol. 60, # 46 SPEC. ISS., p. 10461 - 10468
[5] Dalton Transactions, 2006, # 25, p. 3134 - 3140
  • 3
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Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 7, p. 1939 - 1942
  • 4
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Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 40, p. 13062 - 13063
  • 5
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  • [ 191480-63-4 ]
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Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 7, p. 2903 - 2906
  • 6
  • [ 37942-07-7 ]
  • [ 21436-03-3 ]
  • [ 135616-40-9 ]
Reference: [1] Patent: US6369223, 2002, B2, . Location in patent: Page column 56
  • 7
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  • [ 360784-94-7 ]
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  • [ 886055-61-4 ]
Reference: [1] Journal of Catalysis, 2004, vol. 221, # 1, p. 77 - 84
  • 8
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  • [ 6147-53-1 ]
  • [ 176763-62-5 ]
Reference: [1] Journal of Molecular Catalysis A: Chemical, 1997, vol. 116, # 3, p. 375 - 384
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