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[ CAS No. 35598-05-1 ]

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2D
Chemical Structure| 35598-05-1
Chemical Structure| 35598-05-1
Structure of 35598-05-1 *Storage: {[proInfo.prStorage]}

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Product Details of [ 35598-05-1 ]

CAS No. :35598-05-1MDL No. :MFCD06203918
Formula : C10H12O3 Boiling Point : 265.0±20.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :180.20Pubchem ID :13257269
Synonyms :

Computed Properties of [ 35598-05-1 ]

TPSA : 35.5 H-Bond Acceptor Count : 3
XLogP3 : 2.1 H-Bond Donor Count : 0
SP3 : 0.30 Rotatable Bond Count : 3

Safety of [ 35598-05-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 35598-05-1 ]

  • Upstream synthesis route of [ 35598-05-1 ]
  • Downstream synthetic route of [ 35598-05-1 ]

[ 35598-05-1 ] Synthesis Path-Upstream   1~17

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YieldReaction ConditionsOperation in experiment
100% at 20℃; Reflux To a stirred mixture of 4-methoxy-2-methyl benzoic acid (1.0 g, 6 mmol) and methanol (50 mL) was added thionyl chloride (1.3 mL, 17.8 mmol), dropwise, at room temperature under a nitrogen atmosphere. The reaction mixture was heated at reflux for 3 h. The reaction mixture was allowed to cool at room temperature and concentrated to give a pale yellow liquid. The crude product was purified by flash chromatography over silica with hexanes:ethyl acetate (9:1) to give 1.11 g (100percent) of methyl 2-methyl-4-(methyloxy)benzoate as a colorless liquid. 1H NMR (400 MHz, DMSO-J6): δ 7.81 (d, J = 9 Hz, IH), 6.86 (d, J = 3 Hz, IH), 6.83 (dd, J = 9, 3 Hz, IH), 3.78 (s, 3H), 3.75 (s, 3H), 2.49 (s, 3H). ES-LCMS m/z 181(M + H)+.
98% for 48.00 h; Heating / reflux According to J. Org. Chem. 33: 494 (1968), a mixture of 4-methoxy-2-methylbenzoic acid (20 g, 120 mmol) and [MEOH] (97 mL) containing sulfuric acid [(CONC.,] 0.6 mL) was heated under reflux 48 h. After cooling the mixture was evaporated and the residue diluted with diethyl ether and washed with a saturated sodium hydrogen carbonate solution and brine. The organic phase was then separated and dried over sodium sulphate. After evaporation the residue was distilled through a 8 cm Vigreux column to afford the title compound (21.2 g, 98percent) as a colourless liquid. Bp 60 [C/1] mbar. MS: m/e = 180.3 (M+).
94% With sulfuric acid In water at 65℃; for 18.00 h; 4-Methoxy-2-methyl-benzoic acid methyl esterA solution of 4-Methoxy-2-methyl-benzoic acid (15 g, 90 mmol) in methanol {200 mL) was heated to 65 0C. Sulfuric acid (8.9 g, 90 mmol) was added and the mixture was stirred for 18 h at 65 °C. The reaction was cooled and concentrated and the residual oil was dissolved in ethyl acetate and washed with water, brine, and absorbed onto silica to perform chromatography (10 percent ethyl acetate/hexanes) to yield 4-Methoxy-2-methyl-benzoic acid methyl ester as an oil, (15.3 g, 94 percent). MS: ES M+1: 181.0 (180.1).
84% for 24.00 h; Reflux Benzoic acid (1 equiv) was dissolved in MeOH (1.66 mL per mmol) and H2SO4 (0.07 mL per mmol). The solution was refluxed for 7-24 h before being cooled to rt and concentrated in vacuo. The resulting mixture was dissolved in EtOAc. The organics were washed with an aqueous solution of NaOH (10 percent), combined, dried over MgSO4 and concentrated in vacuo to afford the desired ester.
81% for 3.00 h; Heating / reflux Preparation 67 4-Methoxy-2-methyl-benzoic acid methyl esterTo an ambient temperature suspension of 4-Methoxy-2-methyl-benzoic acid (1.0 g, 6.02 mmol) in MeOH (10 mL) is added thionyl chloride (1.10 mL, 15.04 mmol) dropwise. The reaction mixture is heated to reflux. After 3h, the reaction is concentrated and the residue is partitioned between EtOAc and NaHCO3. The aqueous layer is extracted with EtOAc and the combined organic layers are washed with brine, dried (MgSO4), filtered, and concentrated to yield the title compound (877 mg, 81percent) 1H NMR (400 MHz, CDCl3) δ 7.95-7.91 (m, IH), 6.77-6.72 (m, 2H), 3.86 (s, 3H), 3.84 (s, 3H).

Reference: [1] Patent: WO2009/5998, 2009, A1. Location in patent: Page/Page column 214
[2] Patent: WO2004/14856, 2004, A1. Location in patent: Page 9; 14
[3] Patent: WO2008/20306, 2008, A2. Location in patent: Page/Page column 35
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8561 - 8578
[5] Tetrahedron, 2018, vol. 74, # 2, p. 224 - 239
[6] Patent: WO2007/140183, 2007, A1. Location in patent: Page/Page column 50
[7] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1798 - 1806
[8] Journal of Organic Chemistry, 1968, vol. 33, # 2, p. 494 - 503
[9] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1628 - 1631
[10] Inorganic Chemistry, 2014, vol. 53, # 6, p. 2932 - 2942
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Reference: [1] Patent: WO2011/156518, 2011, A2. Location in patent: Page/Page column 115
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Reference: [1] Patent: US2003/212094, 2003, A1
  • 4
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Reference: [1] Synthesis, 1984, # 6, p. 504 - 506
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Reference: [1] Tetrahedron, 1989, vol. 45, # 18, p. 5791 - 5804
[2] Tetrahedron Letters, 1989, vol. 30, # 1, p. 111 - 112
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  • [ 4685-47-6 ]
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Reference: [1] Synthesis, 1984, # 6, p. 504 - 506
[2] Inorganic Chemistry, 2014, vol. 53, # 6, p. 2932 - 2942
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Reference: [1] Synthesis, 1984, # 6, p. 504 - 506
  • 8
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Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 19, p. 3566 - 3572
  • 9
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Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1798 - 1806
[2] Journal of Organic Chemistry, 1968, vol. 33, # 2, p. 494 - 503
  • 10
  • [ 108-31-6 ]
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Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 21, p. 2201 - 2204
  • 11
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Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 21, p. 2201 - 2204
  • 12
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Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 2, p. 251 - 267
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Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 19, p. 3566 - 3572
  • 14
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Reference: [1] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365
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Reference: [1] Chemische Berichte, 1987, vol. 120, p. 1339 - 1346
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Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 21, p. 2201 - 2204
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