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[ CAS No. 57556-31-7 ] {[proInfo.proName]}

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Chemical Structure| 57556-31-7
Chemical Structure| 57556-31-7
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Product Details of [ 57556-31-7 ]

CAS No. :57556-31-7 MDL No. :MFCD09752667
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :FINKSGWSBJRISB-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :12351986
Synonyms :

Calculated chemistry of [ 57556-31-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.71
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 1.49
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.79

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.61
Solubility : 0.404 mg/ml ; 0.00243 mol/l
Class : Soluble
Log S (Ali) : -3.01
Solubility : 0.163 mg/ml ; 0.000981 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.28
Solubility : 0.876 mg/ml ; 0.00527 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 57556-31-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57556-31-7 ]

* 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 [ 57556-31-7 ]
  • Downstream synthetic route of [ 57556-31-7 ]

[ 57556-31-7 ] Synthesis Path-Upstream   1~11

  • 1
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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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YieldReaction ConditionsOperation in experiment
61% at 80℃; for 5 h; 4.2 g (18 mmol) of 4-iodo-3-methylphenol are dissolved in 90 ml of anhydrous methanol and then placed in a steel reactor. 5 ml (35 mmol) of triethylamine and 400 mg (1.8 mmol) of palladium diacetate are added, the reaction medium is subjected to a carbon monoxide pressure of 3 bar and heated at 80° C. for 5 hours. The medium is then brought to ambient pressure and temperature and then dissolved in dichloromethane and filtered on celite. After evaporation, the residue is purified by chromatography on a silica column. An orange-coloured powder is obtained (m=1.8 g, Y=61 g).
Reference: [1] Patent: US6689922, 2004, B1, . Location in patent: Page column 85-86
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YieldReaction ConditionsOperation in experiment
100% With thionyl chloride In methanol; water; ethyl acetate Example 12
Synthesis of 4-(2',3'-dihydrophytyloxy)-2-methylbenzyl alcohol
To methanol (10 ml) was added dropwise thionyl chloride (1.92 ml, 26.3 mmol) at 0° C., 4-hydroxy-2-methylbenzoic acid (2.00 g, 13.1 mmol) was added, and the mixture was stirred at 60° C. overnight.
After completion of the reaction, the solvent was evaporated, and the residue was dissolved in ethyl acetate (20 ml).
The mixture was washed twice with 5percent aqueous sodium hydrogen carbonate solution (10 ml), once with 1N hydrochloric acid (10 ml), and once with water (10 ml), and the solvent was evaporated to give methyl 4-hydroxy-2-methylbenzoate (2.24 g, yield 100percent).
1H-NMR (300 MHz): δ 2.57 (3H, s, C2-Me), 3.86 (3H, s, -COOMe), 5.68 (1H, s, br, -OH), 6.66-6.72 (2H, m, C3, 5-H), 7.89 (1H, dd, J=2.4, 6.9 Hz, C6-H).
Reference: [1] Patent: US2012/59149, 2012, A1,
[2] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
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YieldReaction ConditionsOperation in experiment
100% at 0 - 60℃; To methanol (10 ml) was added dropwise thionyl chloride (1.92 ml, 26.3 mmol) at 0°C, 4-hydroxy-2-methylbenzoic acid (2.00 g, 13.1 mmol) was added, and the mixture was stirred at 60°C overnight.
After completion of the reaction, the solvent was evaporated, and the residue was dissolved in ethyl acetate (20 ml).
The mixture was washed twice with 5percent aqueous sodium hydrogen carbonate solution (10 ml), once with 1N hydrochloric acid (10 ml), and once with water (10 ml), and the solvent was evaporated to give methyl 4-hydroxy-2-methylbenzoate (2.24 g, yield 100percent).
1H-NMR(300MHz):δ2.57(3H,s,C2-Me),3.86(3H,s,-COOMe), 5.68(1H,s,br,-OH), 6.66-6.72(2H,m,C3,5-H), 7.89(1H,dd,J=2.4,6.9Hz,C6-H).
100% at 0 - 60℃; To methanol (10 ml) was added dropwise thionyl chloride (1.92 ml, 26.3 mmol) at 0°C, 4-hydroxy-2-methylbenzoicacid (2.00 g, 13.1 mmol) was added, and the mixture was stirred at 60°C overnight. After completion of thereaction, the solvent was evaporated, and the residue was dissolved in ethyl acetate (20 ml). The mixture was washedtwice with 5percent aqueous sodium hydrogen carbonate solution (10 ml), once with 1 mol/l hydrochloric acid (10 ml), andonce with water (10 ml), and the solvent was evaporated to give methyl 4-hydroxy-2-methylbenzoate (2.24 g, yield 100percent).
100% at 60℃; To methanol (10 ml) was added dropwise thionyl chloride (1.92 ml, 26.3 mmol) at 0° C., 4-hydroxy-2-methylbenzoic acid (2.00 g, 13.1 mmol) was added, and the mixture was stirred at 60° C. overnight.
After completion of the reaction, the solvent was evaporated, and the residue was dissolved in ethyl acetate (20 ml).
The mixture was washed twice with 5percent aqueous sodium hydrogen carbonate solution (10 ml), once with 1 mol/l hydrochloric acid (10 ml), and once with water (10 ml), and the solvent was evaporated to give methyl 4-hydroxy-2-methylbenzoate (2.24 g, yield 100percent).
95% Heating / reflux a) 4-Hydroxy-2-methyl-benzoic acid methyl ester4-Hydroxy-2-methyl-benzoic acid (4.8 g, 32.0 mmol) was dissolved in MeOH <n="52"/>(40 mL) and catalytic quantity of sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated NaHCO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the product (5.0 g, yield 95?/o) was used without further purification.C9H10O31H-NMR (dmso-d6): 2.43 (3H, s); 3.72 (3H, s); 6.62-6.64 (2H, m); 7.71-7.73 (IH, m); 10.10 (IH, s).
95% Reflux a) 4 -Hydroxy- 2 -methyl- benzoic acid methyl ester; [0182] 4-Hydroxy-2-methyl-benzoic acid (4.8 g, 32.0 mmol) was dissolved in MeOH (40 mL) and catalytic quantity of sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated NaHCO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the product (5.0 g, yield 95percent) was used without further purification.C9H10O3 1H-NMR (dmso-de): 2.43 (3H, s); 3.72 (3H, s); 6.62-6.64 (2H, m); 7.71-7.73 (1H, m); 10.10 (1H, s).
95% Heating / reflux 4-Hydroxy-2-methyl-benzoic acid methyl ester (1.0 g, 6.0 mmol, 1.0 eq) was dissolved in acetone (14 mL), NaI (0.45 g, 3.0 mmol, 0.5 eq) and K2CO3 (1.66 g, 12.0 mmol, 2.0 eq) were added ad the mixture was stirred at room temperature for 20 min. (Bromomethyl)cyclopropane (0.53 mL, 5.4 mmol, 0.9 eq) was added, and the mixture was refluxed for 2 days. The solvent was concentrated under reduced pressure, NaOH 10percent was added, and the crude was extracted with DCM and dried. 0.42 g of title product (yield 32percent) were recovered and used without further purification. C13H16O31H-NMR (CDCl3): 0.23-0.34 (2H, m); 0.52-0.64 (2H, m); 1.15-1.24 (IH, m); 2.52 (3H, s); 3.75 (2H, d, J=7.2 Hz); 3.77 (3H, s); 6.64-6.66 (IH, m); 7.83-7.85 (2H, m).

Reference: [1] Patent: EP2612845, 2013, A1, . Location in patent: Paragraph 0269; 0270
[2] Patent: EP2816053, 2014, A1, . Location in patent: Paragraph 0341
[3] Patent: US9371353, 2016, B2, . Location in patent: Page/Page column 71
[4] Patent: WO2008/87529, 2008, A1, . Location in patent: Page/Page column 51
[5] Patent: WO2010/9290, 2010, A1, . Location in patent: Page/Page column 67
[6] Patent: WO2009/91832, 2009, A1, . Location in patent: Page/Page column 43; 50
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YieldReaction ConditionsOperation in experiment
94.8 %Chromat. With palladium 10% on activated carbon In N,N-dimethyl acetamide at 150℃; for 2 h; Is a starting compound, methyl 2-methyl-4-oxo-2-cyclohexene carboxylate wherein (2), R1 = H, R2 = CH3] N of (730 mg), N-dimethylacetamide (DMA; bp.165 ) solution (4mL) taken up in the reactor, a further 10percent palladium charcoal (50percent moisture; plus 100mg). The amount after the reaction system was reacted for 2 hours while heating and stirring at 0.99 ° C., the amount of the raw material 4-hydroxy-2-methylbenzoic acid methyl in the reaction mixture (target compound (1)) (2) It was analyzed by HPLC. As a result, the yield of the objective compound (1) is 94.8percent residual ratio of the starting compound (2) was 0.1percent.
Reference: [1] Green Chemistry, 2016, vol. 18, # 24, p. 6462 - 6467
[2] Patent: JP2015/63488, 2015, A, . Location in patent: Paragraph 0044-0045; 0047-0048
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Reference: [1] Patent: WO2008/157330, 2008, A1, . Location in patent: Page/Page column 83
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Reference: [1] Organic Letters, 2011, vol. 13, # 4, p. 644 - 647
  • 8
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  • [ 108-39-4 ]
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Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2877 - 2881
  • 9
  • [ 922-67-8 ]
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Reference: [1] Tetrahedron, 1989, vol. 45, # 18, p. 5791 - 5804
  • 10
  • [ 63446-76-4 ]
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Reference: [1] Synthesis, 2004, # 3, p. 401 - 404
  • 11
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Reference: [1] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 2127 - 2133
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