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Chemical Structure| 79831-88-2 Chemical Structure| 79831-88-2

Structure of 79831-88-2

Chemical Structure| 79831-88-2

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Product Details of [ 79831-88-2 ]

CAS No. :79831-88-2
Formula : C28H26O4
M.W : 426.50
SMILES Code : OCC1=CC(OCC2=CC=CC=C2)=C(OCC3=CC=CC=C3)C(OCC4=CC=CC=C4)=C1
MDL No. :MFCD02093503
InChI Key :FWPHSYJOSSBILN-UHFFFAOYSA-N
Pubchem ID :11407668

Safety of [ 79831-88-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 79831-88-2 ]

* 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.

  • Downstream synthetic route of [ 79831-88-2 ]

[ 79831-88-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 70424-94-1 ]
  • [ 79831-88-2 ]
YieldReaction ConditionsOperation in experiment
97.5% With aluminum (III) chloride; sodium tetrahydroborate; In tetrahydrofuran; at 10 - 30℃;Large scale; Tetrahydrofuran (177.6 liters) is charged to a reactor and A1C13 (6.5 kg, 1.0 eq.) is charged at 10-15 C. 2. To the resulting mixture is charged compound IIIa-13-1 (22.2 kg, 1.0 eq.) and then NaBH4 (1.78 kg, 1.0 eq.) at 10-25 C. 3. The resulting reaction mixture is aged for 10 hours at 20-30 C and then additional NaBH4 is charged (1.78 kg, 1.0 eq.) and the mixture stirred for an additional 12 hours. 4. A further 2 equivalents of NaBH4 are charged with subsequent aging of the reaction mixture (12-14 hours) at which time HPLC analysis shows that 5. The reaction mixture is cooled to about 15 C and water is added slowly (55.5 liters). 6. After addition of water, 2 M HCl is added to the mixture and the resulting mixture stirred for a suitable amount of time at 20 C. 7. The layers are settled, the organic layer is separated and the aqueous layer back-extracted with ethyl acetate. 8. The combined organic layers are washed with 6% NaHC03 and then 20% brine. 9. The combined organic layer and wash is then concentrated to about 2.5 volumes under vacuum at 40-50 C and heptane is charged (about 67 liters). 10. The mixture is further concentrated to about 3 volumes under vacuum. 11. The mixture is filtered and the cake washed with heptane. 12. The cake is dried under vacuum at 35-45 C to obtain 20.1 kg of IIIa-13-1-2 as an off-white sold in 97.5% yield and 96.5% purity.
95% With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h;Heating / reflux; A mixture of methyl gallate 9 (10 g, 53 mmol) and potassium carbonate (45 g, 320 mmol) in DMF (120 mL) was treated with benzyl bromide (210 mmol, 25.7 mL) and stirred at 40 C. under an argon atmosphere for 24 h. The reaction mixture was filtered and the filtrate evaporated to dryness. The residue was dissolved in minimum amount of methylene chloride and diluted with an equal volume of hexanes and loaded onto a short silica gel pad in a sintered glass funnel. The silica was eluted with hexanes (300 mL) to remove excess benzyl bromide and the eluant discarded. The product was then eluted with methylene chloride: hexanes (1:1, 300 mL) followed by methylene chloride (500 mL) and the eluants combined and evaporated to afford pure benzyl product 10 as an off-white solid (100% yield). 1H NMR (300 MHz, CDCl3): delta 3.88 (s, 3H, CH3), 5.11 and 5.13 (2s, 6H, OCH2), 7.35-7.41 (m, 17H, Ar-H). [0119] To a solution of 3,4,5-tribenzyl-methyl gallate 10 (10 g, 22 mmol) in dry tetrahydrofuran (75 mL) was added solid lithium aluminum hydride (1.25 g, 33 mmol) in small portions. The suspension was heated to reflux under argon for 2 h. The reaction was cooled to 0 C. and carefully quenched with the dropwise addition of water. The slurry was then extracted with ethylacetate/hexanes. The organic solution was dried with saturated brine, followed by anhydrous magnesium sulfate, filtered and evaporated to afford the pure alcohol 11 as a white solid (8.9 g, 95% yield). 1H NMR (300 MHz, CDCl3): delta 4.6 (d, 2H, CH2), 5.04 and 5.11 (2s, 6H, OCH2), 6.67 (s, 2H, 2,6-Ar-H), 7.25-7.43 (m, 15H, Ar-H). [0120] To a solution of 3,4,5-tribenzyloxy-benzyl alcohol 11 (8.9 g, 21 mmol) in methylene chloride (200 mL) at 0 C. was added pyridinium chlorochromate (5.43 g, 25 mmol) in small portions with vigorous stirring. The cooling was discontinued and reaction stirred at room temperature for 4 h. The dark brown suspension was filtered over a long pad of silica gel in a sintered glass funnel, and eluted with methylene chloride, until all the pure product eluted out. The organic filtrate was evaporated down to give the pure product 12 as a soft white solid (8.1 g, 91.5% yield). 1H NMR (300 MHz, CDCl3): delta 5.16 (s, 6H, OCH2), 7.18 (s, 2H, 2,6-Ar-H), 7.26-7.41 (m, 15H, Ar-H), 9.80 (s, 1H, CHO).
90% With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h;Inert atmosphere; Reflux; Lithium aluminum hydride (0.809 g, 0.0213 mole) was suspended in 40 mL of freshly distilled THF in a dry three-neck round-bottom flask under nitrogen atm. (AB)3 G1-COOCH3 (9 g, 0.0198 mole) was dissolved in 50 mL of freshly distilled THF and added drop wise to the lithium aluminum hydride solution. The reaction mixture was refluxed with stirring for 2 hours. The THF solution was cooled to room temperature and transferred to a beaker. Water was added drop wise to the vigorously stirred THF solution until the gray color of the lithium aluminum hydride was disappeared and a white solid was formed which is filtered and washed with THF. Excess solvent was removed under reduced pressure and the crude product was recrystallized from 95% methanol/water mixture to get the pure product ((AB)3 G1-CH2OH) (7.6 g, 90%); 1H NMR (400 MHz, CDCl3) delta: 4.6 (s, CH2OH, 2H), 5.09 (s, ArCH2O, 2H), 5.15 (s, ArCH2O, 4H), 6.72 (s, ArH, 2H), 7.30-7.48 (m, PhH, 15H); 13C NMR (100 MHz, CDCl3) delta: 65.42, 71.22, 75.26, 106.46, 127.45, 127.83, 127.90, 128.18, 128.52, 128.62, 136.66, 137.13, 137.81, 137.87, 153.02.
With lithium aluminium tetrahydride; In tetrahydrofuran; EXAMPLE 5b 3,4,5-Trisbenzyloxybenzyl Alcohol A solution of 20.0 g (0.044 mol) of <strong>[70424-94-1]3,4,5-trisbenzyloxybenzoic acid methyl ester</strong> in 100 ml of THF is added dropwise with vigorous stirring, over a period of 60 minutes at room temperature, to a suspension of 4.00 g (0.11 mol) of lithium alanate in 100 ml of THF, in the course of which the temperature rises to 65 C. (reflux). After a further 2 hours at reflux, excess lithium alanate is cautiously hydrolyzed, and the product is isolated in customary manner by extraction with methylene chloride. Amorphous powder, yield 12.0 g (64% of theory). 1H-NMR (CDCl2): 1.70 (t, 1H, OH), 4.45 (d, 2H, CH2OH), 4.95 (s, 2H, OCH2), 5.00 (s, 4H, OCH2), 6.55 (s, 2H, arom. H), 7.15-7.40 (m, 15H, arom. H)

 

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