Methyl 2,5-dihydroxybenzoate
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Methyl 2,5-dihydroxybenzoate
structure -
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CAS No:
2150-46-1
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Formula:
C8H8O4
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Chemical Name:
Methyl 2,5-dihydroxybenzoate
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Synonyms:
Benzoic acid,2,5-dihydroxy-,methyl ester;Gentisic acid,methyl ester;Methyl 2,5-dihydroxybenzoate;Methyl gentisate;2,5-Dihydroxybenzoic acid methyl ester;Methoxycarbonylhydroquinone;NSC 618316;2-Methoxycarbonyl-1,4-Benzenediol;2-(Methoxycarbonyl)hydroquinone
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CAS No:
Methyl 2,5-dihydroxybenzoate Basic Attributes
168.15
168.15
218-427-8
LS28B004KM
618316
DTXSID80175841
29182900
Characteristics
66.8
2.6
1.4±0.1 g/cm3
86 °C
55 °C @ Press: 0.01 Torr
137.6±15.8 °C
1.588
0.000893mmHg at 25°C
Safety Information
NONH for all modes of transport
3
36/37/38
26-36
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (33.33%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 133 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Methyl 2,5-dihydroxybenzoate Use and Manufacturing
Compound 1 (2, 5-Dihydroxybenzoic acid) (5.00 g, 32.5 mmol) was dissolved in methanol (33 mL) and concentrated sulphuric acid (5 mL) added drop wise. The reaction mixture was heated at ref lux for 16 h. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The residue was treated with saturated aqueous NaHCO3 until pH 7 was reached. The product was extracted with ethyl acetate (50 mL x 3) and the combined organic layer was washed with brine (20 mL), dried (Mg504), filtered and the filtrate was evaporated to afford the product as a light brown powder(5.13 g, 94percent). 1H NMR (CDCI3) O 10.35 (5, 1H), 7.29 (d, J= 3.2 Hz, 1H), 7.02 (dd, J= 8.7, 3.2 Hz, 1H), 6.89 (d, 8.7 Hz, 1H), 4.69 (5, 1H), 3.95 (5, 1H); 13C NMR (CDCI3) O 170.1, 155.8, 147.6, 124.0, 118.5, 114.7, 112.1, 52.4; HRMS (ESI): [M-H] calcd. for C8H704 167.0344, found 167.0359.To a 250 mL flask equipped with a magnetic stirrer, 15.4 g (0.1 mol) of 2, 5-dicumylbenzoic acid, 100 mL of methanol and 10 mL of concentrated sulfuric acid were added and the temperature was raised to 65 ° C and refluxed for 12 hours.The reaction was cooled and poured into 1000 mL of water. The precipitate was collected by filtration, washed three times with saturated sodium hydrogencarbonate solution, and washed with water in a vacuum oven at 60 ° C for 24 hours to obtain a compound represented by the formula (4) = 1) 14. 8 g, yield 88.1percentGeneral procedure: Thionyl chloride (1.16 g, 1.5 equiv) was added drop-wise to a solution of acid (1.0 g, 1.0 equiv) in the corresponding alcohol (15 ml) at 0&d eg;C. The solution was refluxed under a nitrogen atmosphere until all starting material was consumed (TLC monitoring). Then the solvent was removed under vacuo and the residue was purified by silica gel column chromatography eluting with ethyl acetate/n-hexane to afford the corresponding carboxylic esters.#10;A solution of gentisic acid (10 mmol) and sulfuric acid (0.5 mL) in methanol (20 mL) was refluxed for 2h, then diluted with 10percent aq Na5 g (32.5 mmol) of 2, 5-dihydroxybenzoic acid was well dissolved in 60 mL of methanol, 41 mL (162 mmol) of hydrogen chloride 4M dioxane solution was slowly added thereto while stirring. After the reaction for 12 hours, solvent was removed and the resulting solution was extracted with water and ethyl acetate. An organic layer thus separated was neutralized with sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered off, and then solvent was removed to give 3.2g of the title compound in a yield of 59percent.NMR: Methyl 2, 5-dihydroxybenzoate (19) To a solution of 2, 4-dihydroxybenzoic acid (20.0 g, 0.13 mol) in MeOH (200 mL) was added concentrated H
Organic synthesis, pharmaceutical synthesis intermediate, can be used to synthesize flecainide
Computed Properties
Molecular Weight:168.15
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:168.04225873
Monoisotopic Mass:168.04225873
Topological Polar Surface Area:66.8
Heavy Atom Count:12
Complexity:168
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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