* 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.
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1 h;
As previously reported in the literature [31] , a solution of 4-vinylbenzoic acid (500 mg, 3.37 mmol) in Et2O (25 mL) was drop-wise added to a 0 °C slurry of LiAlH4 (758 mg, 19.97 mmol) in THF (80 mL). The reaction mixture was warmed to room temperature and stirred for 1 h. The reaction was quenched via the following workup: 256 μL of water added slowly, 512 μL of 10 wtpercent NaOH solution, and 768 μL of water. The mixture was stirred vigorously until a white solid was formed. The crude reaction mixture was filtered, and the supernatant was dried (anhydrous Na2SO4), and concentrated in vacuo. The resulting oil was purified by silica gel column chromatography using an elutant of hexane:EtOAc, (4:1) to provide alcohol 1 (280 mg, 62percent) as colourless oil. All the physical and spectral data were in accordance with the literature [31] . 1H NMR (CDCl3, 500 MHz) δ: 4.66 (s, 2H), 5.24 (d, J = 11.5 Hz, 1H) 5.73 (d, J = 18.5 Hz, 1H) 6.69-6.75 (dd, J = 11.0, 6.5 Hz, 1H) 7.31 (d, J = 8.0 Hz, 2H) 7.39 (d, J = 8.0 Hz, 2H).
62%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1 h;
A solution of 4-vinylbenzoic acid (500 mg, 3.37 mmol) in Et20 (25 mL) was added dropwise to a 0°C slurry of L1AIH4 (758 mg, 19.97 mmol) in THF (80 mL) (K.S. Bloome, et al, Palladium-catalyzed Heck-type reactions of alkyl iodides, J Am Chem Soc 133 (2011) 20146-20148, 2011) The reaction mixture was warmed to room temperature and stirred for one hour. The reaction was quenched via the following workup: 256 μ, water added slowly, followed by the addition of 512 μ, of 10 wt percent NaOH solution, and then 768 μ, water. The mixture was stirred vigorously until a white solid was formed. The crude reaction mixture was filtered, and the supernatant was dried (anhydrous a2S04), and concentrated in vacuo. The resulting oil was purified by silica gel column chromatography using an elutant of Hexane:EtOAc, (4: 1) to provide alcohol 1 (shown in Figure 2) (280 mg,62percent) as a colorless oil. NMR (CDC13, 500 MHz) δ: 4.66 (s, 2H), 5.24 (d, J= 11.5 Hz, 1H) 5.73 (d, J= 18.5 Hz, 1H) 6.69-6.75 (dd, J= 11.0, 6.5 Hz, 1H) 7.31 (d, J= 8.0 Hz, 2H) 7.39 (d, J= 8.0 Hz, 2H).
Reference：
[1] Journal of the American Chemical Society, 2011, vol. 133, # 50, p. 20146 - 20148
[2] Reactive and Functional Polymers, 2014, vol. 81, # 1, p. 54 - 60
[3] Patent: WO2015/73882, 2015, A1, . Location in patent: Page/Page column 10-11
2
[ 1791-26-0 ]
[ 1074-61-9 ]
Yield
Reaction Conditions
Operation in experiment
66%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; tris[3,5-bis(trifluoromethyl)phenyl]-borane In 1,4-dioxane at 25℃; for 12 h; Glovebox
General procedure: In a glovebox, aldehydes (0.25 mmol) and the Hantzsch ester 1 (95 mg, 0.38 mmol) were added to asolution of tris[3,5-bis(trifluoromethy)phenyl]borane (9) (8.1 mg, 12.5 μmol) in 1 mL of anhydrous1,4-dioxane. The reaction mixture was stirred at 25 or 100 C for 12 h. An internal standard (biphenylor mesitylene) was added to the reaction mixture and filtrated through a cotton plug. The resultingsolution was analyzed with gas chromatography.
Reference：
[1] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
[2] Synlett, 2015, vol. 26, # 14, p. 2037 - 2041
[3] Green Chemistry, 2009, vol. 11, # 9, p. 1313 - 1316
3
[ 1592-20-7 ]
[ 1074-61-9 ]
Reference：
[1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 1, p. 54 - 60
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 24, p. 5152 - 5161
[3] Journal of the American Chemical Society, 2017, vol. 139, # 40, p. 13969 - 13972
[4] Macromolecules, 2005, vol. 38, # 11, p. 4698 - 4704
[5] Tetrahedron, 2005, vol. 61, # 51, p. 12026 - 12032
[6] Chemistry - A European Journal, 2007, vol. 13, # 8, p. 2369 - 2376
[7] Tetrahedron, 2005, vol. 61, # 51, p. 12160 - 12167
[8] Journal of Materials Chemistry, 2011, vol. 21, # 19, p. 6956 - 6961
[9] Polymer, 2011, vol. 52, # 15, p. 3318 - 3324
[10] Journal of Materials Chemistry C, 2014, vol. 2, # 12, p. 2251 - 2258
[11] Biomacromolecules, 2019, vol. 20, # 1, p. 546 - 557
4
[ 1592-12-7 ]
[ 1074-61-9 ]
Reference：
[1] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 4, p. 780 - 791
[2] Macromolecules, 2005, vol. 38, # 11, p. 4698 - 4704
[3] Tetrahedron, 2005, vol. 61, # 51, p. 12026 - 12032
[4] Chemistry - A European Journal, 2007, vol. 13, # 8, p. 2369 - 2376
[5] Journal of the American Chemical Society, 1947, vol. 69, p. 1905
[6] Tetrahedron, 2005, vol. 61, # 51, p. 12160 - 12167
[7] European Journal of Organic Chemistry, 2009, # 18, p. 2943 - 2946
[8] Chemical Communications, 2010, vol. 46, # 33, p. 6051 - 6053
[9] Polymer, 2011, vol. 52, # 15, p. 3318 - 3324
5
[ 873-75-6 ]
[ 1074-61-9 ]
Reference：
[1] Journal of Organic Chemistry, 2006, vol. 71, # 26, p. 9681 - 9686
poly(4-styryldiphenylphosphine-co-[4-vinylbenzyl alcohol]-co-1,4-bis[4-vinylphenoxy]butane); monomer(s): 4-styryldiphenylphosphine; 4-vinylbenzyl alcohol; 1,4-bis(4-vinylphenyl)butane[ No CAS ]
With phosphorus tribromide; In diethyl ether; at 0 - 20℃; for 2h;Inert atmosphere;
Using a reaction scheme adapted from literature [32] , phosphorous tribromide (18.4 g, 6.4 mL, 68 mmol) dissolved in diethyl ether (10 mL) was added to alcohol 1 (5.9 g, 44.3 mmol) in Et2O (500 mL) at 0 °C under N2. After 1 h, additional phosphorous tribromide (18.4 g, 6.4 mL, 68 mmol) was added. The reaction mixture was stirred for 1 h at room temperature and subsequently cooled to 0 °C. Water (100 mL) was slowly added. The solution was extracted with Et2O, and the Et2O layer was washed with saturated NaHCO3, brine and dried over MgSO4. The crude product was purified by silica gel column chromatography using a hexane:EtOAc, (70:30) elutant system to obtain product vinyl benzyl bromide 2. 1H NMR (CDCl3, 500 MHz) delta: 4.48 (s, 2H), 5.26 (dd, J = 11.0, 1.0 Hz, 1H) 5.76 (dd, J = 17.6, 1.0 Hz, 1H) 6.69-6.75 (dd, J = 17.6, 11.0 Hz, 1H), 7.32 (d, J = 8.0 Hz, 2H) 7.41 (d, J = 8.0 Hz, 2H). UV-Vis [chloroform, lambdamax(epsilon)]: 215 nm, 260 nm.
With phosphorus tribromide; In diethyl ether; at 0 - 20℃; for 2h;Inert atmosphere;
Using a reaction scheme adapted from O. Shimomura, et al, Synthesis and application of polytetrahydrofuran-grafted polystyrene (PS-PTHF) resin supports for organic synthesis, Tetrahedron 61 (2005) 12160-12167, phosphorous tribromide (PBr3) (18.4 g, 6.4 ml, 68 mmol) dissolved in ethyl ether (10 ml) was added to <strong>[1074-61-9]4-vinylbenzyl alcohol</strong> (5.9 g, 44.3 mmol) in Et20 (500 ml) at 0°C under N2. After 1 hour, additional PBr3 (18.4 g, 6.4 ml, 68 mmol) was added. The reaction mixture was stirred for 1 hour at room temperature and subsequently cooled to 0°C. Water (100 ml) was slowly added. The solution was extracted with Et20, and the Et20 layer was washed with aqueous NaHC03, brine and dried with MgS04. The crude product was purified by silica gel column chromatography using a hexane:EtOAc, (70:30) eluent system to obtain product vinyl benzyl bromide. XH NMR (CDC13, 500 MHz) £4.48 (s, 2H), 5.26(d, 1H) 5.76(d, 1H) 6.69-6.75(q, 1H) 7.32(d, 2H) 7.41 (d, 2H). UV-vis [chloroform, max(8)]:215, 260.
With bromine; triphenylphosphine; In dichloromethane;
Step A 1-Bromomethyl-4-vinyl-benzene. Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, <strong>[1074-61-9]4-vinylbenzyl alcohol</strong> (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1*) followed by brine (1*). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3*), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) delta 7.32-7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H).
With bromine; triphenylphosphine; In dichloromethane;
Step A 1-Bromomethyl-4-vinyl-benzene Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, <strong>[1074-61-9]4-vinylbenzyl alcohol</strong> (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1*) followed by brine (1*). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3*), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) delta7.32-7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H).
poly(ethylene glycol), α-terminated with 4-vinylbenzyloxy group, ω-terminated with 2-carboxylatoethylcarboxy group, potassium salt, Mn 1.8E3 Da; monomer(s): 4-vinylbenzyl alcohol; ethylene oxide; succinic anhydride[ No CAS ]
EXAMPLE 15 Preparation of mono-2-{2-[2-(4-Vinylbenzylthio)ethoxy]ethylthio}ethyl succinate This compound was prepared by procedures analogous to those of Example 2 except substituting the intermediate 2-{2-[2-(4-vinylbenzylthio)ethoxy]ethylthio}ethanol in place of the p-vinylbenzyl alcohol: m.p. of 58°-60° C. Yield of 88percent of white solid. Analysis calculated for C19 H29 O5 S2: C, 57.26, H, 6.50, S, 16.89. Found: C, 57.24, H, 6.87, S, 15.88. 1 H NMR(CDCl3), 2.65 (m, 10H, STR19 CH2 S--CH2, CH2 S), 3.65 (m, 4H, CH2 O--CH2), 3.7 (s, 2H, ArCH2 S), 4.3 (t, 2H, STR20 5.25+5.75 (AB quartet, 2H, CH2 =), 6.75 (m, 1H, CH=), 7.32 (m, 4H, ArH's), 9.6 (broad s, 1H, CO2 H).
25
[ 1074-61-9 ]
[ 53715-97-2 ]
[ 139441-07-9 ]
Yield
Reaction Conditions
Operation in experiment
With 2-(Dimethylamino)pyridine; In chloroform;
EXAMPLE 1 Preparation of Mono-p-vinylbenzyl Glutarate To a solution of p-vinylbenzyl alcohol (76 g, 0.56 mole) and glutaric anhydride (70 g, 0.61 mole) in chloroform (600 ml) was added dimethylaminopyridine (75 g, 0.61 mole) in chloroform (250 ml) in dropwise fashion at room temperature over 15 minutes. Heat was evolved with the temperature rising to 45° C. The reaction mixture was stirred for an additional hour at ambient temperature. It was then washed three times with hydrochloric acid (5percent, 200 ml) and twice with saturated sodium chloride (250 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed to provide the crude acid (130 g, 94percent yield). A small sample was chromatographed to provide pure monomer. Analysis calculated for C14 H16 O4: C, 67.73, H, 6.50, Found: C, 66.82, H, 6.42.
poly(acenaphthylene-co-5-hydroxymethylstyrene)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
2,2'-azobis(isobutyronitrile); In acetic acid butyl ester; at 75℃; for 7h;
A separable flask equipped with a thermometer was charged with acenaphthylene (6 parts), 4-hydroxymethyl styrene (5 parts), n-butyl acetate (44 parts), and azobisisobutyronitrile (48 parts) in a nitrogen atmosphere. The mixture polymerized at 75°C for seven hours while stirring. The reaction mixture was diluted with n-butyl acetate (100 parts) and the organic layer was washed with a large amount of a mixed solvent of water and methanol (weight ratio 1:2). The solvent was evaporated to obtain a Polymer (IV) with an Mw of 1,200.
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; tris[3,5-bis(trifluoromethyl)phenyl]-borane; In 1,4-dioxane; at 25℃; for 12h;Glovebox;
General procedure: In a glovebox, aldehydes (0.25 mmol) and the Hantzsch ester 1 (95 mg, 0.38 mmol) were added to asolution of tris[3,5-bis(trifluoromethy)phenyl]borane (9) (8.1 mg, 12.5 mumol) in 1 mL of anhydrous1,4-dioxane. The reaction mixture was stirred at 25 or 100 C for 12 h. An internal standard (biphenylor mesitylene) was added to the reaction mixture and filtrated through a cotton plug. The resultingsolution was analyzed with gas chromatography.
With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 1h;
As previously reported in the literature [31] , a solution of 4-vinylbenzoic acid (500 mg, 3.37 mmol) in Et2O (25 mL) was drop-wise added to a 0 C slurry of LiAlH4 (758 mg, 19.97 mmol) in THF (80 mL). The reaction mixture was warmed to room temperature and stirred for 1 h. The reaction was quenched via the following workup: 256 muL of water added slowly, 512 muL of 10 wt% NaOH solution, and 768 muL of water. The mixture was stirred vigorously until a white solid was formed. The crude reaction mixture was filtered, and the supernatant was dried (anhydrous Na2SO4), and concentrated in vacuo. The resulting oil was purified by silica gel column chromatography using an elutant of hexane:EtOAc, (4:1) to provide alcohol 1 (280 mg, 62%) as colourless oil. All the physical and spectral data were in accordance with the literature [31] . 1H NMR (CDCl3, 500 MHz) delta: 4.66 (s, 2H), 5.24 (d, J = 11.5 Hz, 1H) 5.73 (d, J = 18.5 Hz, 1H) 6.69-6.75 (dd, J = 11.0, 6.5 Hz, 1H) 7.31 (d, J = 8.0 Hz, 2H) 7.39 (d, J = 8.0 Hz, 2H).
62%
With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 1h;
A solution of 4-vinylbenzoic acid (500 mg, 3.37 mmol) in Et20 (25 mL) was added dropwise to a 0C slurry of L1AIH4 (758 mg, 19.97 mmol) in THF (80 mL) (K.S. Bloome, et al, Palladium-catalyzed Heck-type reactions of alkyl iodides, J Am Chem Soc 133 (2011) 20146-20148, 2011) The reaction mixture was warmed to room temperature and stirred for one hour. The reaction was quenched via the following workup: 256 mu, water added slowly, followed by the addition of 512 mu, of 10 wt % NaOH solution, and then 768 mu, water. The mixture was stirred vigorously until a white solid was formed. The crude reaction mixture was filtered, and the supernatant was dried (anhydrous a2S04), and concentrated in vacuo. The resulting oil was purified by silica gel column chromatography using an elutant of Hexane:EtOAc, (4: 1) to provide alcohol 1 (shown in Figure 2) (280 mg,62%) as a colorless oil. NMR (CDC13, 500 MHz) delta: 4.66 (s, 2H), 5.24 (d, J= 11.5 Hz, 1H) 5.73 (d, J= 18.5 Hz, 1H) 6.69-6.75 (dd, J= 11.0, 6.5 Hz, 1H) 7.31 (d, J= 8.0 Hz, 2H) 7.39 (d, J= 8.0 Hz, 2H).
With C32H44N4O8P2Pd; potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 12h;Inert atmosphere; Schlenk technique;
General procedure: A Schlenk tube was charged with readily prepared complex 6 (2 mol percent) under a nitrogen atmosphere. Then styrene (104 mg, 1 mmol), K2CO3 (276 mg, 2 mmol) and dimethyl formamide (1 mL) were added at 25 °C. The reaction mixture was stirred under a nitrogen atmosphere. To this solution, bromobenzene (0.157 mg, 1 mmol) was then added with a syringe and the reaction mixture was heated at 60 °C in an oil bath for 12 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with EtOAc, and filtered through a pad of Celite. The collected filtrate was then concentrated using a rotary evaporator, and the residue was purified by flash chromatography (10percent EtOAc/hexane), which yielded 172 mg (96percent) of trans-stilbene.
2-bromo-1-(4-(hydroxymethyl)phenyl)ethanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With water; hydrogen bromide; In dimethyl sulfoxide; at 60℃; for 12h;Schlenk technique;
A 25 mL Schlenk reaction tube was charged with 67 mg of p-hydroxymethylstyrene, 101 mg of 48percent aqueous hydrobromic acid,Dimethyl sulfoxide (2 mL), and the mixture was stirred at 60 ° C for 12 hours. After the completion of the reaction, 15 mL of ethyl acetate was added to quench the reaction, and 5 mL of brine was addedThe organic phase was separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were separated by column chromatography to give 2-bromo-1- (4-hydroxymethylYl-phenyl) -ethanol 96 mg in 83percent yield.
With boron trifluoride diethyl etherate; In diethyl ether; for 6h;
Add boron trifluoride-diethyl ether (3 drops) to DHA (426 mg, 1.50 mmol, 1.00 equiv) in diethyl ether (30 mL)(4-Vinylphenyl)methanol (370 mg, 2.76 mmol, 1.84 eq.).After 6 hours, the reaction mixture was saturatedThe aqueous NaHCO3 solution was quenched and dried (MgSO4).Filter and concentrate the filtrate.The residue was obtained and purified with ethyl acetate /hexane (1:10)The product was obtained as a colorless oil (198 mg, 33percent).
To a 250mL of 3 necked flask equipped with a magnetic stirrer was added sodium hydride (3.58g of 60percent dispersion in oil, 89mmol) under a nitrogen atmosphere. Heptane (5OmL) was added to the flask and stirring continued for 15 minutes, after which time the heptane was removed and 1 OOmL of THF was added in its stead. The mixture was cooled with ice-water. 4- Vinylbeiizyl alcohol (lOg, 74mmol) in THF (lOmL) was added and stirring continued for lh at the same temperature. Epiclon 85OCRP (25.34g, 74mrnol) in THF (25mL) was added tothe mixture and stirring continued for 5h at room temperature. Any excess NaH was quenched by the slow addition of water. The mixture was extracted with ethyl acetate (300mL), and the organic layer was washed 4 times with deionized water and dried over anhydrous Na2SO4. After filtration, 5g of silica gel and 4g of sillitin were added and the washed and dried mixture stirred for 1 h. The mixture was filtered and washed with 5OmL of ethyl acetate. 2000ppm oftbutylcatechol was added and the solvent evaporated to yield the styrenyl epoxy resin as a viscous liquid.
4-vinylbenzyl 2-bromo-2-methylpropanoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With pyridine; In dichloromethane; at 0℃;
Preparation of 4-(2-bromoizobutyroylmethl) styrene was carried out according to a procedure adapted from literature [11]. For this purpose, to a solution of <strong>[1074-61-9]4-vinylbenzyl alcohol</strong> (4.956g, 37mmol) and pyridine (3.219, 40.7mmol) in 50mL dry dichloromethane was added 2-bromoisobutyryl bromide (8.506g, 37mmol) dropwise using an addition funnel for 20minat 0C. The solution was stirred for 5h. The precipitate (pyridinium salt) was filtered off.
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