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[ CAS No. 25081-39-4 ]

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2D
Chemical Structure| 25081-39-4
Chemical Structure| 25081-39-4
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Product Details of [ 25081-39-4 ]

CAS No. :25081-39-4MDL No. :MFCD00077971
Formula : C10H12O2 Boiling Point : 242.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :164.20Pubchem ID :32786
Synonyms :

Computed Properties of [ 25081-39-4 ]

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : 2.5 H-Bond Donor Count : 0
SP3 : 0.30 Rotatable Bond Count : 2

Safety of [ 25081-39-4 ]

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

Application In Synthesis of [ 25081-39-4 ]

  • Upstream synthesis route of [ 25081-39-4 ]
  • Downstream synthetic route of [ 25081-39-4 ]

[ 25081-39-4 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 499-06-9 ]
  • [ 67-56-1 ]
  • [ 25081-39-4 ]
YieldReaction ConditionsOperation in experiment
87% at 55 - 60℃; for 4 h; Autoclave General procedure: benzoic acid (Table 3, entry 1) (1.0 g,0.0081 mol), bromobenzene (0.125 g, 0.0081 mol), 10percent palladium on carbon(50percent wet) (0.2 g) and methanol (3 mL) were placed in autoclave vessel. Autoclave was pressurized with 1–2 bar of nitrogen followed by 1–2 bar of hydrogen gas and then put under the desired pressure of hydrogen (5–6 bar).The reaction mixtures are then warmed to 55–60 C temperature and stirredfor 4 h at 300 rpm. After reaction, the catalyst was filtered through celite bed.Filtrate was added with water (30 mL). The reaction mixture was extracted with isopropyl acetate (2 15 mL). The combined organic layers were washedwith 5percent aqueous sodium bicarbonate solution (2 15 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated under vacuum togive of methyl benzoate product
Reference: [1] Helvetica Chimica Acta, 1996, vol. 79, # 7, p. 1967 - 1979
[2] Journal of Organic Chemistry, 2006, vol. 71, # 19, p. 7205 - 7213
[3] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
[4] European Journal of Organic Chemistry, 2009, # 26, p. 4480 - 4485
[5] Tetrahedron Letters, 2013, vol. 54, # 42, p. 5690 - 5694
[6] Journal of Medicinal Chemistry, 1980, vol. 23, # 11, p. 1198 - 1201
[7] Angewandte Chemie - International Edition, 1998, vol. 37, # 13-14, p. 1846 - 1850
[8] Tetrahedron, 2009, vol. 65, # 22, p. 4298 - 4303
[9] Tetrahedron Letters, 2009, vol. 50, # 49, p. 6803 - 6806
[10] Organic and Biomolecular Chemistry, 2012, vol. 10, # 5, p. 1088 - 1092
[11] Comptes Rendus Chimie, 2015, vol. 18, # 12, p. 1320 - 1327
[12] Synlett, 2017, vol. 28, # 11, p. 1373 - 1377
[13] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 44, p. 11797 - 11805
  • 2
  • [ 499-06-9 ]
  • [ 25081-39-4 ]
YieldReaction ConditionsOperation in experiment
90% With sulfuric acid In methanol Example 1
Preparation of methyl-3,5-dimethyl-benzoate
A solution of 3,5-dimethyl benzoic acid (25 g, 0.17 mol) in methanol (250 ml) was treated with sulfuric acid (1 ml, cat. amount) and heated to reflux.
After 10 hours, the solution was cooled to room temperature, concentrated to approximately 1/2 volume and poured into 200 ml of crushed ice.
The mixture was extracted twice with 200 ml portions of diethyl ether.
The organic phase was extracted with saturated aqueous sodium carbonate, dried over magnesium sulfate, and concentrated under reduced pressure.
The resulting solid was recrystallized from hexanes to yield the product (24.5 g, 90percent yield) as volatile white plates. mp=32°-35° C. (lit. mp=35°-36° C.)
90% With sulfuric acid In methanol EXAMPLE 1
Preparation of methyl-3,5-dimethyl-benzoate:
A solution of 3,5-dimethyl benzoic acid (25 g, 0.17 mol) in methanol (250 ml) was treated with sulfuric acid (1 ml, cat. amount) and heated to reflux.
After 10 hours, the solution was cooled to room temperature, concentrated to approximately 1/2 volume and poured into 200 ml of crushed ice.
The mixture was extracted twice with 200 ml portions of diethyl ether.
The organic phase was extracted with saturated aqueous sodium carbonate, dried over magnesium sulfate, and concentrated under reduced pressure.
The resulting solid was recrystallized from hexanes to yield the product (24.5 g, 90percent yield) as volatile white plates. mp=32°-35° C. (lit. mp=35°-36° C.)
Reference: [1] Patent: US5342934, 1994, A,
[2] Patent: US5599926, 1997, A,
[3] Bulletin de la Societe Chimique de France, 1948, p. 593,596
  • 3
  • [ 4749-37-5 ]
  • [ 866918-70-9 ]
  • [ 25081-39-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2005, vol. 44, # 31, p. 4914 - 4917
  • 4
  • [ 67-56-1 ]
  • [ 5779-95-3 ]
  • [ 25081-39-4 ]
YieldReaction ConditionsOperation in experiment
89% for 3 h; Reflux General procedure: The starting aldehydematerials (1 mmol) were dissolved in MeOH (5 mL),and Oxone (1 mmol) and 10 mol percent of In(OTf)3 were added atroom temperature. The reaction mixture was heated at reflux,and was monitored for completion by TLC. After the reactionmixture was filtered, the filtrate was condensed using arotary evaporator. Flash column chromatography on silica gelfurnished the corresponding products, which were confirmedby spectroscopy.
Reference: [1] Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 8, p. 870 - 872
  • 5
  • [ 4919-37-3 ]
  • [ 25081-39-4 ]
Reference: [1] Patent: US6090836, 2000, A,
  • 6
  • [ 51329-15-8 ]
  • [ 80-48-8 ]
  • [ 25081-39-4 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 73, p. 10180 - 10183
  • 7
  • [ 67-56-1 ]
  • [ 108-67-8 ]
  • [ 25081-39-4 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 19, p. 5122 - 5126
  • 8
  • [ 67-56-1 ]
  • [ 6613-44-1 ]
  • [ 25081-39-4 ]
YieldReaction ConditionsOperation in experiment
2.98 g for 2 h; Reflux To the crude acid chloride (3), methanol (25.0 ml) was added,and heated under the reflux conditions for 2 h. The excess methanolwas evaporated in vacuo. The ester (4) was crystallized fromhexane yielding 2.98 g (55percent), mp. = 26–29 C.
Reference: [1] Bulletin de la Societe Chimique de France, 1948, p. 593,596
[2] Journal of Molecular Structure, 2013, vol. 1048, p. 172 - 178
  • 9
  • [ 556-96-7 ]
  • [ 25081-39-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 23, p. 5033 - 5040
  • 10
  • [ 22445-41-6 ]
  • [ 25081-39-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 23, p. 5033 - 5040
  • 11
  • [ 186581-53-3 ]
  • [ 499-06-9 ]
  • [ 25081-39-4 ]
Reference: [1] Magnetic Resonance in Chemistry, 2004, vol. 42, # 10, p. 844 - 851
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 23, p. 5033 - 5040
  • 12
  • [ 675-09-2 ]
  • [ 624-48-6 ]
  • [ 50919-64-7 ]
  • [ 25081-39-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 811 - 813
  • 13
  • [ 675-09-2 ]
  • [ 624-49-7 ]
  • [ 50919-64-7 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 811 - 813
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