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[ CAS No. 40663-68-1 ] {[proInfo.proName]}

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Chemical Structure| 40663-68-1
Chemical Structure| 40663-68-1
Structure of 40663-68-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 40663-68-1 ]

CAS No. :40663-68-1 MDL No. :MFCD00014133
Formula : C10H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :TYNJQOJWNMZQFZ-UHFFFAOYSA-N
M.W :162.19 Pubchem ID :95942
Synonyms :

Safety of [ 40663-68-1 ]

Signal Word:Warning Class:
Precautionary Statements:P280 UN#:
Hazard Statements:H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 40663-68-1 ]

* 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 [ 40663-68-1 ]
  • Downstream synthetic route of [ 40663-68-1 ]

[ 40663-68-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 40663-68-1 ]
  • [ 5736-85-6 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen In methanol at 20℃; for 2 h; General procedure: The mixture of the substrate (0.250 mmol), 0.5percent Pd/MS3A or 0.5percent Pd/MS5A (10 wt percent of the substrate) and MeOH (1 mL) was stirred under H2 atmosphere (balloon) at room temperature. After a given period, the reaction mixture was filtered through a membrane filter (Millipore, Millex.(R).-LH, 0.45 mm), and the filtrate was concentrated in vacuo to produce the corresponding reduced product.
Reference: [1] Synthetic Communications, 2007, vol. 37, # 24, p. 4381 - 4388
[2] Tetrahedron, 2012, vol. 68, # 39, p. 8293 - 8299
[3] Tetrahedron, 2006, vol. 62, # 51, p. 11925 - 11932
[4] RSC Advances, 2016, vol. 6, # 57, p. 52495 - 52499
[5] Organometallics, 2010, vol. 29, # 9, p. 2098 - 2103
[6] Organic Process Research and Development, 2012, vol. 16, # 6, p. 1230 - 1234
  • 2
  • [ 40663-68-1 ]
  • [ 10035-16-2 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 32, p. 7746 - 7755
  • 3
  • [ 123-08-0 ]
  • [ 109-64-8 ]
  • [ 40663-68-1 ]
  • [ 3722-80-3 ]
  • [ 17954-81-3 ]
YieldReaction ConditionsOperation in experiment
77% With potassium carbonate In acetonitrile at 20 - 60℃; for 3 - 4 h; Industry scale The exemplary process of the invention is shown schematically in Figure 1.0 Step (a): 4-(3-Bromopropyloxy)benzaldehyde (Compound 1)A dry Belatech glass reactor (30L) was flushed with argon and charged with 4- hydroxybenzaldehyde (588g, 4.8MoIe), 1,3-dibromopropane (4.976kg, 24.6MoIe) and anhydrous acetonitrile (24L) under argon. Dried powdered 5 potassium carbonate (1.66kg, 12MoIe) was added in portions to the stirred solution. The suspension was stirred at 55-60°C and monitored by gas chromatography and cooled (ice bath) to room temperature as soon as the 4- hydroxybenxaldehyde had been consumed (3-4hr). Solids were removed by filtration (2L Buechner funnel) and washed with dry acetonitrile (3 x 300 mL). ,0 The combined solvents were reduced in volume by rotary evaporation (bath temperature 400C) and then the excess of 1,3-dibromopropane was removed by <n="21"/>high, vacuum distillation (bath temperature 400C). Crude product was obtained as a bright yellow oil (1350g). The crude product was purified by column chromatography under argon using 10 kg silica gel, eluting with a mixture of heptane:ethyl acetate (75L; 9:1, by vol.) followed by a mixture of heptane: ethyl acetate (HL; 4:1, by vol.). After 5OL of the first eluant had been eluted, fractions (50OmL) of eluate were collected and their purities checked by TLC. The fractions containing pure product were combined and dried by rotary evaporation (bath temperature 4O0C) to yield pure product as a colourless oil. Yield: 90Og (3.7MoIe, 77percent). TLC: Rf = 0.38 (A). GC: purity > 95 percent (rt = 12.7min). 1H-NMR analysis: δH (300MHz5 CD3OD): 2.35 (quint, 3J Iληz, 2H), 3.58 (t, 3J 7.4Hz, 2H), 4.18 (t, 3J 7.4Hz, 2H), 6.95, 7.85 (2 x d, 3J 8.5Hz; 4H), 9.85 (s, IH).Comments:Acetone and THF as reaction solvents were also investigated and found to give inferior outcomes to acetonitrile.It is important to secure highly pure product in this step. Product contaminated with the elimination product leads in the next step to the corresponding porphyrin by-product containing an unsaturated propene group.The product is air sensitive. Formation of the oxidation product (the carboxylic acid) was observed during workup. Due to the air sensitivity of the product, column chromatography should be carried out under an argon atmosphere and the bottles of the collected fractions should be kept closed.Two main by-products, an elimination product and a dimer, formed in the reaction. By TLC analysis, three compounds were observed: 4-allyloxy- benzaldehyde (Rf - 0.42), product (Rf = 0.38) and 4-[3-(4- foπnylphenoxy)propyloxy]benzaldehyde (Rf= 0.20). <n="22"/>By GC analysis four compounds were detected: excess 1,3-dibromopropane (rt = 4.525min); elimination product (rt = 9.725min); product (rt = 12.858min) and the dimer (rt = 19.75min).
Reference: [1] Patent: WO2007/74340, 2007, A1, . Location in patent: Page/Page column title page; 18-20; Sheet 1/2
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