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Product Details of Methyl 2,4-dihydroxybenzoate

CAS No. :2150-47-2
Formula : C8H8O4
M.W : 168.15
SMILES Code : C1=C(C(=CC(=C1)O)O)C(OC)=O
MDL No. :MFCD00002276
InChI Key :IIFCLXHRIYTHPV-UHFFFAOYSA-N
Pubchem ID :16523

Safety of Methyl 2,4-dihydroxybenzoate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335-H412
Precautionary Statements:P261-P273-P305+P351+P338

Application In Synthesis of Methyl 2,4-dihydroxybenzoate

* 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 [ 2150-47-2 ]
  • Downstream synthetic route of [ 2150-47-2 ]

[ 2150-47-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 2150-47-2 ]
  • [ 75-26-3 ]
  • [ 943519-37-7 ]
YieldReaction ConditionsOperation in experiment
45% With aluminum (III) chloride In dichloromethane at 50℃; for 24 h; Inert atmosphere A mixture of compound 6 (3.9g, 23.0mmol), 2-bromopropane (4.3mL, 46.0mmol), and aluminum chloride (6.1g, 46.0mmol) in CH2Cl2 was stirred at 50°C for 24h, equipped with a refluxing condenser under argon. 2-Bromopropane (4.3mL, 46.0mmol) was added to the reaction mixture three times every 6h. The mixture was neutralized with 10percent NaOH to pH 5, concentrated under reduced pressure, and then extracted with ethyl aceatate. The organic layer was washed with saturated NaHCO3 solution three times, dried over Na2SO4, concentrated under reduced pressure, and purified by column to afford compound 16 in 45percent yield. Rf=0.21 (1:4 ethyl acetate: hexane). 1H NMR (400MHz, CDCl3) δ 10.8 (s, 1H), 7.64 (s, 1H), 6.34 (s, 1H), 5.50 (s, 1H), 3.90 (s, 3H), 3.15–3.08 (m, 1H), 1.25 (d, J=10.8Hz, 6H). 13C NMR (100MHz, CDCl3) δ 170.7, 161.6, 159.6, 128.1, 127.1, 105.7, 103.2, 52.2, 26.7, 22.8.
45% With aluminum (III) chloride In dichloromethane at 50℃; for 24 h; Inert atmosphere Compound 7 was synthesized in the same manner as in Reaction Scheme 1 above.Compound 6 (3.9 g, 23.0 mmol), 2-bromopropane (4.3 mL, 46.0 mmol) and aluminum chloride (6.1 g, 46.0 mmol) were added in CH2Cl2 and stirred in a reflux condenser at 50 C for 24 hours under argon.2-Bromopropane (4.3 mL, 46.0 mmol) was added to the reaction mixture three times every 6 hours. The mixture was then neutralized by the addition of 10percent NaOH (pH 5), concentrated under reduced pressure and extracted with ethyl acetate.The organic layer was washed three times with saturated NaHCO3 solution, dried over Na2SO4 and concentrated under reduced pressure. The concentrate was then purified by silica gel chromatography to give compound 7 in 45percent yield.
45% With aluminum (III) chloride In dichloromethane at 50℃; for 30 h; Methylene chloride (CH2Cl2), the compound 4 (3.9 g, 23.0 mmol), 2-bromopropane (4.3 mL, 46.00 mmol) and aluminum chloride (6.1 g, , 46.0 mmol) were added and stirred at 50 ° C for 24 hours. 4.3 mL (46.0 mmol) of 2-bromopropane was then added to the reaction mixture three times for a total of 6 hours. The mixture was neutralized with 10percent sodium hydroxide until the pH reached 5, concentrated in a reduced pressure environment and extracted with ethyl acetate. The organic layer was washed three times with saturated NaHCO3 solution, dried in the presence of Na2SO4 and concentrated again under reduced pressure. It was then purified on a silica gel column to give compound 5 with a yield of 45percent. Rf = 0.21 (1: 4 ethyl acetate: hexane).
45% With aluminum (III) chloride In dichloromethane at 50℃; for 24 h; Inert atmosphere; Microwave irradiation 21.
Methyl 2,4-dihydroxy-5-isopropylbenzoate (12)
Compound 6 (3.9 g, 23.0 mmol), 2-bromopropane (4.3 mL, 46.0 mmol) and aluminum chloride (6.1 g, 46.0 mmol) were dissolved in CH2Cl2 and then stirred under argon at 50° C. for 24 hours with a reflux condenser under a microwave irradiation (Biotage Initiator).
3-Bromopropane (4.3 ml, 46.0 mmol) was added to the reaction mixture three times every 6 hours.
The mixture was neutralized with 10percent NaOH to pH 5, concentrated under pressure and extracted with ethyl acetate.
The organic layer was washed with saturated NaHCO3 solution three times, dried over Na2SO4, concentrated under pressure and purified by column to obtain Compound 12 in a yield of 45percent.
Rf=0.21 (1:4 ethyl acetate:hexane).
1H NMR (400 MHz, CDCl3) δ 10.8 (s, 1H), 7.64 (s, 1H), 6.34 (s, 1H), 5.53 (s, 1H), 3.92 (s, 3H), 3.15-3.08 (m, 1H), 1.25 (d, J=10.8 Hz, 6H).
13C NMR (100 MHz, CDCl3) δ 170.7, 161.6, 159.6, 128.1, 127.1, 105.7, 103.2, 52.2, 26.7, 22.8

References: [1] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 1069 - 1080.
[2] Patent: KR101641829, 2016, B1, . Location in patent: Paragraph 0043-0044; 0051-0055.
[3] Patent: KR101789269, 2017, B1, . Location in patent: Paragraph 0046; 0048; 0054; 0055.
[4] Patent: US2019/31620, 2019, A1, . Location in patent: Paragraph 0190; 0191; 0192; 0193; 0194; 0290; 0291; 0292.
[5] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 390 - 401.
 

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