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(5-Methoxy-1,3-phenylene)dimethanol
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[ CAS No. 19254-84-3 ] {[proInfo.proName]}

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Chemical Structure| 19254-84-3
Chemical Structure| 19254-84-3
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Product Details of [ 19254-84-3 ]

CAS No. :19254-84-3 MDL No. :MFCD00182463
Formula : C9H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 168.19 Pubchem ID :-
Synonyms :

Safety of [ 19254-84-3 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 19254-84-3 ]

* 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.

  • Downstream synthetic route of [ 19254-84-3 ]

[ 19254-84-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 20319-44-2 ]
  • [ 19254-84-3 ]
YieldReaction ConditionsOperation in experiment
95% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16.25h; Inert atmosphere;
90% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Reflux; 3,5-Bis(hydroxymethyl)anisole. To a mixture of LiAlH4 (306 mg, 8.05 mmol) in anhydrous THF (20 mL) was added drop wise a solution of 5-methoxy-isophthalic acid dimethyl ester (600 mg, 2.68 mmol) in THF (20 mL). The resulting mixture was refluxed for 2 h and then stirred at room temperature overnight. The reaction was quenched subsequently by adding ethyl acetate (1.0 mL), ethanol (1.0 mL) and water (1 mL). The reaction mixture was filtered and the filtrate was evaporated under reduced pressures to give 3,5-bis(hydroxymethyl) anisole (405 mg, 90%). 1H NMR (CDCl3, 400 MHz) δ 6.84 (s, 1H) 6.74 (s, 2H) 4.53 (s, 4H) 3.75 (s, 3H) 3.14 (br, 2H) and ESI-MS: m/z 191.36 ([M+Na]+). The 1H NMR data are in agreement with the ones reported in literatures. 5
87% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h;
86% With lithium aluminium tetrahydride In diethyl ether
With lithium aluminium tetrahydride In diethyl ether
With sodium hydroxide In tetrahydrofuran; water 1 3,5-Bis(hydroxymethyl)anisole (15): 3,5-Bis(hydroxymethyl)anisole (15): Referring to 3,5-bis(hydroxymethyl)anisole (15) was synthesised according to a method described by A. B. Pangborn, et al., (Organometallics 1996, 15, 1518-1520). A solution of dimethyl 5-methoxyisophthalate (7.0 g, 31 mmol) in THF was added to a suspension of lithium aluminum hydride (6.0 g, 158 mmol) at 0(C. The reaction was maintained at room temperature for 30 min. The reaction was then quenched with 7 mL of water, 7 mL of 15% NaOH, and 30 mL of water. Filtration of aluminum salts and evaporation of the filtrate gave the product as a white solid. Recrystallization from chloroform provided white needles (4.61 g, 27.4 mmol, 88%). 1H NMR (CDCl3) (6.90 (s, 1H), 6.81 (s, 2H), 4.62 (s, 4H), 3.79 (s, 3H).

Reference： [1]Helbing, Tim; Carraro, Caterina; Francke, Alexander; Sosic, Alice; De Franco, Michele; Gandin, Valentina; Göttlich, Richard; Gatto, Barbara [ChemMedChem, 2020, vol. 15, # 21, p. 2040 - 2051]
[2]Yu, Xi-Hui; Peng, Chen-Chen; Sun, Xiao-Xiao; Chen, Wen-Hua [European Journal of Medicinal Chemistry, 2018, vol. 152, p. 115 - 125]
[3]Fan, Heli; Sun, Huabing; Peng, Xiaohua [Chemistry - A European Journal, 2018, vol. 24, # 30, p. 7671 - 7682]
[4]Boldt, Peter; Bruhnke, Detlev [Journal fur Praktische Chemie - Chemiker-Zeitung, 1994, vol. 336, # 2, p. 110 - 114]
[5]Zimmerman,H.E.; Jones,G. [Journal of the American Chemical Society, 1970, vol. 92, p. 2753 - 2761] Boekelheide,V.; Griffin,R.W. [Journal of Organic Chemistry, 1969, vol. 34, p. 1960 - 1961]
[6]Current Patent Assignee: SCRIPPS RESEARCH - US2002/115092, 2002, A1
  • 2
  • [ 46331-50-4 ]
  • [ 19254-84-3 ]
YieldReaction ConditionsOperation in experiment
62% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 21.0h;Reflux; To a stirred suspension of LiAlH4 (3.0 g, 100 mmol) in THF (50 mL) was added dropwise a THF (100 mL) solution of <strong>[46331-50-4]5-methoxyisophthalic acid</strong> (4.8 g, 24 mmol)during 1 h at 0 C. The suspension was stirred at reflux for 20 h. To the solution wasslowly added ice water (10 mL) at 0 C followed by 10% HCl aq until reaching a pH<7. The mixture was extracted with Et2O (40 mL x 5). The combined organic layers werewashed with brine (40 mL x 5), dried over Na2SO4, filtered, and concentrated in vacuoto give 5-methoxy-1,3-bis(hydroxymethyl)benzene (7c, 2.50 g, 62% yield).To a stirred CHCl3 (30 mL) solution of 5-methoxy-1,3-bis(hydroxymethyl)benzene (7c,0.78 g, 4.6 mmol) was added PBr3 (3.7 g, 1.3 mL, 13.6 mmol), and the resultingsolution was stirred at room temperature for 16 h. To the solution was added sat NH4Claq (15 mL). The mixture was extracted with Et2O (30 mL x 3). The combined organiclayers were washed with brine (30 mL x 3), dried over Na2SO4, filtered, andconcentrated in vacuo to give 5-methoxy-1,3-bis(bromomethyl)benzene (8c, 1.2 g, 90%yield). To a stirred mixture of NaH (1.01 g, 42 mmol) in THF (5 mL) was slowly added THF(100 mL) solution of 5-methoxy-1,3-bis(hydroxymethyl)benzene (7c, 0.70 g, 4.2mmmol), and the solution was stirred at reflux for 2 h. To the solution was added a THF(150 mL) solution of 5-methoxy-1,3-bis(bromomethyl)benzene (8c, 1.2 g, 4.2 mmol),and the resulting solution was stirred at reflux for 2 days. To the solution was added icewater (20 mL) at<10 C. The mixture was extracted with Et2O (50 mL x 3). Thecombined organic layers were washed with brine (50 mL x 3), dried over Na2SO4,filtered, and concentrated in vacuo, giving a residue that was subjected to silica gelcolumn chromatography (three times, each eluent; CHCl3, CHCl3:AcOEt = 20:1,CHCl3:AcOEt = 10:1) followed by recrystallization from CH2Cl2/hexane gave6,15-dimethoxy-2,11-dioxa[3.3]metacyclophane (6c, 0.02 g, 2% yield). Colorless solid;mp 123-125 C;
Reference： [1]Chemistry Letters,2017,vol. 46,p. 1357 - 1360

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