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Chemical Structure| 57-55-6
Chemical Structure| 57-55-6
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Product Details of [ 57-55-6 ]

CAS No. :57-55-6 MDL No. :
Formula : C3H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DNIAPMSPPWPWGF-UHFFFAOYSA-N
M.W : 76.09 Pubchem ID :1030
Synonyms :
1,2-Propylene glycol;Propylene glycol;1,2-(RS)-Propanediol
Chemical Name :1,2-Propanediol

Calculated chemistry of [ 57-55-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 18.86
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.0
Log Po/w (XLOGP3) : -0.92
Log Po/w (WLOGP) : -0.64
Log Po/w (MLOGP) : -0.63
Log Po/w (SILICOS-IT) : -0.54
Consensus Log Po/w : -0.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.33
Solubility : 164.0 mg/ml ; 2.16 mol/l
Class : Highly soluble
Log S (Ali) : 0.55
Solubility : 272.0 mg/ml ; 3.58 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.56
Solubility : 275.0 mg/ml ; 3.61 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 57-55-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57-55-6 ]

* 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 [ 57-55-6 ]

[ 57-55-6 ] Synthesis Path-Upstream   1~46

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Reference: [1] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837
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Reference: [1] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837
  • 3
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Reference: [1] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837
  • 4
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Reference: [1] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837
  • 5
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  • [ 123-32-0 ]
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Reference: [1] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0052-0053; 0089
[2] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0056-0057; 0089
[3] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0058-0059; 0089
[4] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0060-0061; 0089
[5] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0076-0077; 0089
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Reference: [1] RSC Advances, 2014, vol. 4, # 54, p. 28664 - 28672
  • 7
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  • [ 78-90-0 ]
  • [ 21655-48-1 ]
  • [ 2815-34-1 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 34, p. 6752 - 6759
[2] European Journal of Organic Chemistry, 2012, # 34, p. 6752 - 6759
  • 8
  • [ 57-55-6 ]
  • [ 78-90-0 ]
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  • [ 2815-34-1 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 34, p. 6752 - 6759
[2] European Journal of Organic Chemistry, 2012, # 34, p. 6752 - 6759
  • 9
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Reference: [1] ChemCatChem, 2017, vol. 9, # 14, p. 2768 - 2783
  • 10
  • [ 6298-19-7 ]
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  • [ 38240-21-0 ]
Reference: [1] Patent: US5814651, 1998, A,
  • 11
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  • [ 65673-85-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 4, p. 823 - 830
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  • [ 68696-86-6 ]
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Reference: [1] Synthesis (Germany), 2014, vol. 46, # 10, p. 1380 - 1388
  • 13
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Reference: [1] Patent: US2007/287865, 2007, A1, . Location in patent: Page/Page column 12
[2] Patent: US2007/287865, 2007, A1, . Location in patent: Page/Page column 13
  • 14
  • [ 57-55-6 ]
  • [ 123-32-0 ]
  • [ 6168-72-5 ]
  • [ 14008-30-1 ]
  • [ 78-90-0 ]
  • [ 108-49-6 ]
Reference: [1] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0052-0053; 0089
[2] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0056-0057; 0089
[3] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0058-0059; 0089
[4] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0060-0061; 0089
[5] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0076-0077; 0089
  • 15
  • [ 57-55-6 ]
  • [ 6168-72-5 ]
  • [ 14008-30-1 ]
  • [ 78-90-0 ]
Reference: [1] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0072-0073; 0089
[2] Patent: CN104693038, 2017, B, . Location in patent: Paragraph 0074-0075; 0089
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Reference: [1] Chemistry Letters, 2014, vol. 43, # 6, p. 822 - 824
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Reference: [1] RSC Advances, 2014, vol. 4, # 54, p. 28664 - 28672
  • 18
  • [ 57-55-6 ]
  • [ 35320-23-1 ]
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YieldReaction ConditionsOperation in experiment
14.8 % ee
Stage #1: With titanium(IV) isopropylate; n-Dodecylamine; (R,R)-TADDOL In diphenylether at 90℃; for 1 h;
Stage #2: at 90℃; for 0.166667 h;
Example 26. Separation of rac.-1,2-propanediol using a chiral selector generated from (4R,5R)-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane and Ti(O-isopropyl)4 in the presence of dodecylamine6.5 mmol (3.0 g) of (4R,5R)-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane, 6.5 mmol (1.83 g) of titanium tetraisopropoxide and 13 mmol (2.41 g) of dodecylamine are put into 20 ml of diphenyl ether in a glove box. The resulting clear solution is stirred under protective gas at 90° C. for 60 min. This is followed by addition of 26 mmol (1.98 g) of rac.-1,2-propanediol and stirring for a further 10 min. The resulting isopropanol is then distilled out under about 20 mbar. Subsequently, 2.3 g of a mixture of diphenyl ether and 1,2-propanediol is distilled out at 1 mbar and 90° C. The (S)-1,2-propanediol enantiomeric excess determined by gas chromatography (BGB-174S, TFA derivatization) was 14.8percent.
Reference: [1] Patent: US2009/30235, 2009, A1, . Location in patent: Page/Page column 14
  • 19
  • [ 57-55-6 ]
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Reference: [1] Journal of the Chemical Society, 1953, p. 2224,2231,[2] Journal of the Chemical Society, 1954, p. Errata
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Reference: [1] Patent: EP1258483, 2002, A1, . Location in patent: Example 1-2
[2] Patent: EP1258483, 2002, A1, . Location in patent: Page 5
[3] Patent: EP1247805, 2002, A1, . Location in patent: Example 1-2
[4] Patent: US6372924, 2002, B1, . Location in patent: Example 1
[5] Patent: US6372924, 2002, B1, . Location in patent: Example 20
[6] Patent: US6372924, 2002, B1, . Location in patent: Example 16-19
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  • [ 616-38-6 ]
YieldReaction ConditionsOperation in experiment
13.2% at 130℃; for 8 h; Autoclave; High pressure General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min.
12.5% at 130℃; for 8 h; Autoclave; High pressure General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min.
5.8% at 130℃; for 8 h; Autoclave; High pressure General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min.
23% at 130℃; for 8 h; Autoclave; High pressure General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min.
7.8% at 130℃; for 8 h; Autoclave; High pressure General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min.

Reference: [1] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236
[2] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236
[3] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236
[4] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236
[5] Journal of Chemical Research, 2011, vol. 35, # 11, p. 654 - 656,3
[6] Journal of Chemical Research, 2011, vol. 35, # 11, p. 654 - 656,3
[7] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236
[8] Frontiers of Chemistry in China, 2011, vol. 6, # 1, p. 21 - 30
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Reference: [1] Catalysis Today, 2014, vol. 227, p. 87 - 95
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YieldReaction ConditionsOperation in experiment
52.4% at 130℃; for 8 h; Autoclave; High pressure General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min.
Reference: [1] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236
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Reference: [1] Patent: WO2016/99789, 2016, A1, . Location in patent: Paragraph 0057; 0058; 0059; 0060
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YieldReaction ConditionsOperation in experiment
11.8 %Chromat. at 60℃; for 12 h; Autoclave; Supercritical conditions General procedure: PO synthesis reaction from propylene in presence of ex situ H2O2, as oxidizing agent, were performed in a 3 mL round bottom glass reactor in which the stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of TS-1 catalyst (2.5 mg), methanol (1.2 g), and propylene (9 mmol) were added, followed by the addition of the oxidant, 35percent wt H2O2 in water (0.4 mmol). Then, the mixture was heated at 60°C, and the reaction was monitored for 5 h. The experiments for the direct synthesis of PO with in situ generated H2O2 were carried out in a 15 mL stainless steel reactor which contained a relief valve, for safety. The stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of catalyst (15 mg), acidity inhibitor (ammonium acetate, 0.01 g) and co-solvent (0.2 gof different co-solvents) were added to the reactor, followed by the addition of propylene (2 mmol) and CO2, reaching carbon dioxide vapor pressure (>55 bar). Oxygen and hydrogen were added to the reactor by means of high pressure burettes, and then the reactor was heated up to desired temperature (ranging from room temperature to 80°C, according each experiment). The reaction experiments were carried out for 5 h, unless otherwise stated. At the end of the reaction, the reactor was cooled down and the pressure was slowly released by venting, accumulating the gaseous mixture in an inert gas sampling bag. 3-pentanone was used forrecovering any product that could be retained on the reactor walls. The amount of formed products, i.e., propylene oxide, acetone, propionaldehyde, acrolein, isopropanol, 1-methoxy-2-propanol (MP1), 2-methoxy-1-propanol (MP2), propylene glycol (PG) and propylene carbonate were analyzed using a Shimadzu Gas chro-matograph GC-2010 Plus provided with FID detector and 20 m length, 0.10 mm ID, 0.10 m df. Permabond FFAP column. The amounts of propane and unreacted propylene, oxygen and hydrogen were analyzed using a Bruker 450-GC which contains two different independent channels. The first one is provided with a thermal conductivity detector (TCD) and three different columns: Hayesep N (0.5 m length), Hayesep Q (1.5 m length) and molsieve 13× (1.2 m length), using argon as carrier. The second one is provided with two different flame ionization detectors (FID) and three different columns: capillary column CP-Wax (1 m length and 0.32 mm ID), CP-Porabond Q (25 m length and 0.32 mm ID) and CP-Wax (5 m length and 0.32 mm ID).
Reference: [1] Patent: EP1359148, 2003, A1, . Location in patent: Page/Page column 6-7
[2] Patent: US7470801, 2008, B1, . Location in patent: Page/Page column 7
[3] Patent: US7470801, 2008, B1, . Location in patent: Page/Page column 7
[4] Patent: US7470801, 2008, B1, . Location in patent: Page/Page column 7
[5] Applied Catalysis A: General, 2016, vol. 523, p. 73 - 84
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Reference: [1] Patent: US2004/6239, 2004, A1, . Location in patent: Page 5-6
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Reference: [1] Patent: US2007/173655, 2007, A1, . Location in patent: Page/Page column 4
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Reference: [1] Catalysis Today, 2012, vol. 187, # 1, p. 168 - 172
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Reference: [1] Journal of Physical Organic Chemistry, 1995, vol. 8, # 2, p. 121 - 126
[2] Journal of Physical Organic Chemistry, 1995, vol. 8, # 2, p. 121 - 126
[3] Journal of Physical Organic Chemistry, 1995, vol. 8, # 2, p. 121 - 126
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Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 4, p. 943 - 950
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YieldReaction ConditionsOperation in experiment
41% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 2 h; The 1,2-propanediol (5g, 65.7mmol) and NaH (3.29g, 82 . 0mmol) dissolved in N, N-dimethylformamide (70 ml) in. In 0 °C add benzyl bromide (7.82 ml, 65 . 7mmol), then stirring 2 hours. After the reaction is completed, water and ethyl acetate extraction. Organic layer is dried with anhydrous sodium sulfate, filtered and concentrated. Purification of the residue column chromatographying. Generating title compound (4.45g, 41percent).
41% With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2 h; 1,2-propanediol (5 g, 65.7 mmol) and NaH (3.29 g, 82.0 mmol) were dissolved in N,N-dimethylformamide (70 mL). benzyl bromide (7.82 mL, 65.7 mmol) was added at 0° C., followed by stirring for 2 hr. After reaction was finished, extraction was performed with water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by a column chromatography. The title compound (4.45 g, 41percent) was produced. 1H-NMR (CDCl3, Varian 400 MHz): δ 1.15 (3H, d, J=6.4 Hz), 2.37 (1H, brs), 3.28 (1H, dd, J=9.4, 8.2 Hz), 3.47 (1H, dd, J=9.4, 3.0 Hz), 3.98-4.02 (1H, m), 4.56 (2H, s), 7.25-7.38 (5H, m).
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