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[ CAS No. 80407-64-3 ]

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2D
Chemical Structure| 80407-64-3
Chemical Structure| 80407-64-3
Structure of 80407-64-3 *Storage: {[proInfo.prStorage]}

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Product Details of [ 80407-64-3 ]

CAS No. :80407-64-3MDL No. :MFCD25562935
Formula : C13H18O5 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :254.28Pubchem ID :16063391
Synonyms :

Computed Properties of [ 80407-64-3 ]

TPSA : 54 H-Bond Acceptor Count : 5
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.46 Rotatable Bond Count : 9

Safety of [ 80407-64-3 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 80407-64-3 ]

  • Upstream synthesis route of [ 80407-64-3 ]
  • Downstream synthetic route of [ 80407-64-3 ]

[ 80407-64-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 627-42-9 ]
  • [ 139-85-5 ]
  • [ 80407-64-3 ]
YieldReaction ConditionsOperation in experiment
96.4% With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 105 - 110℃; Inert atmosphere the 121g (leq) ELTA 1200ml and dimethylformamide (DMF) was stirred clear solution; sequentially added 323g (4eq) 2- chloroethyl methyl ether, 944g (8eq) of anhydrous potassium carbonate and 23.6gTetrabutylammonium bromide; purged with nitrogen three times,Under nitrogen, the reaction was heated to 105~110 ° C 13~14h; the filter cake was rinsed DCM until the filtrate was colorless; the combined filtrate was concentrated under reduced pressure to a fraction distilled off; the residue was added DCM, cooled to room temperature , washed with 3Ν K0H, the DCM phase was separated, washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to 45 ° C to give 210g oil ELTB, yield 96.4percent
70% With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 14 h; To a solution of 3,4-dihydroxybenzaldehyde (10 g, 72.5 mmol) (Aldrich) in DMF (200 mL) was added 2-chloroethyl methyl ether (16.5 mL, 181.2 mmol) (Aldrich), potassium carbonate (50 g, 362.3 mmol) and a catalytic amount of potassium iodide (Aldrich).
The reaction mixture was heated at 85° C. for 14 hours.
The reaction mixture was cooled down, diluted with EtOAc and washed with brine.
The organic phase was dried over anhydrous sodium sulfate, evaporated to afford 3,4-bis-(2-methoxy-ethoxy)-benzaldehyde as an oil and was used in the next step without further purification. (Yield 11 g, 70percent).
Reference: [1] Patent: CN105566233, 2016, A, . Location in patent: Paragraph 0015; 0052
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 4, p. 435 - 440
[3] Patent: US2012/184548, 2012, A1, . Location in patent: Page/Page column 23; 24
  • 2
  • [ 6482-24-2 ]
  • [ 139-85-5 ]
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YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2 h; a) 3,4-bis (2-methoxyethoxy) benzaldehyde:; To 3, 4-dihydroxy benzaldehyde of the formula Il (25g, 0.1811 mole), potassium carbonate (6Og, 0.4347 mole) in N, N-dimethyl formamide (120ml) was added 2-bromoethylmethyl ether (50.4g, 0.3625 mole). The mixture was stirred at 1000C for 2 hours, cooled to room temperature, filtered inorganics. The clear filtrate was concentrated under vacuum and the residue was dissolved in methylene chloride, washed with water and dried over calcium chloride. ^Evaporation yielded 3,4-bis (2-methoxyethoxy) benzaldehyde of formula III (45g, 98percent).NMR spectrum (CDCI3): δ 3.46 (s, 6H), 3.81 (m, 4H), 4.22 (m, 4H), 7.00(d, 1 H), 7.43(s, 1 H), 7.45(d, 1 H) and 9.83(s, 1 H).
98% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2 h; a) 3,4-bis (2-methoxyethoxy) benzaldehyde:; To 3, 4-dihydroxy benzaldehyde of the formula Il (25g, 0.1811 mole), potassium carbonate (6Og, 0.4347 mole) in N, N-dmethyl formamide (120ml) was added 2-bromoethylmethyl ether (50.4g, 0.3625 mole). The mixture was stirred at 1000C for 2 hours, cooled to room temperature, filtered inorganics. The clear filtrate was concentrated under vacuum and the residue was dissolved in methylene chloride, washed with water and dried over calcium chloride. Evaporation yielded 3,4-bis (2- methoxyethoxy) benzaldehyde of formula III (45g, 98percent).NMR spectrum (CDCI3): δ 3.46 (s, 6H), 3.81 (m, 4H), 4.22 (m, 4H), 7.00(d, 1 H), 7.43(S1 1H)1 7.45(d, 1 H) and 9.83(s, 1 H).
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[2] Patent: WO2007/138612, 2007, A2, . Location in patent: Page/Page column 9
[3] Patent: WO2007/138613, 2007, A2, . Location in patent: Page/Page column 10
[4] Organic Letters, 2017, vol. 19, # 11, p. 3005 - 3008
  • 3
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  • [ 80407-64-3 ]
Reference: [1] Patent: US2010/298351, 2010, A1, . Location in patent: Page/Page column 35
  • 4
  • [ 36865-41-5 ]
  • [ 139-85-5 ]
  • [ 80407-64-3 ]
Reference: [1] Patent: WO2007/71348, 2007, A1, . Location in patent: Page/Page column 83-84
  • 5
  • [ 121-33-5 ]
  • [ 80407-64-3 ]
Reference: [1] Patent: CN105566233, 2016, A,
  • 6
  • [ 80407-64-3 ]
  • [ 179688-29-0 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[2] Synthetic Communications, 2014, vol. 44, # 3, p. 346 - 351
[3] Patent: CN105566233, 2016, A,
[4] Patent: CN107445907, 2017, A,
  • 7
  • [ 80407-64-3 ]
  • [ 236750-65-5 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[2] Patent: CN107445907, 2017, A,
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