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Product Details of [ 168899-58-9 ]

CAS No. :168899-58-9
Formula : C10H10O4
M.W : 194.18
SMILES Code : CC(=O)OC1=CC=CC(C(O)=O)=C1C
MDL No. :MFCD00957176
InChI Key :LHVJUPHCLWIPLZ-UHFFFAOYSA-N
Pubchem ID :3798557

Safety of [ 168899-58-9 ]

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

Application In Synthesis of [ 168899-58-9 ]

* 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.

  • Downstream synthetic route of [ 168899-58-9 ]

[ 168899-58-9 ] Synthesis Path-Downstream   1~37

  • 1
  • [ 168899-58-9 ]
  • 3-hydroxy-2-methyl-benzoic acid <i>N</i>'-<i>tert</i>-butyl-<i>N</i>'-(3,5-dimethyl-benzoyl)-hydrazide [ No CAS ]
  • 2
  • [ 168899-58-9 ]
  • 3-(3-acetoxy-2-methyl-benzoylamino)-2-hydroxy-3-thiophen-2-yl-propionic acid ethyl ester [ No CAS ]
  • 3
  • [ 168899-58-9 ]
  • [ 755012-12-5 ]
  • 4
  • [ 168899-58-9 ]
  • (R)-3-[(2S,3S)-2-Hydroxy-3-(3-hydroxy-2-methyl-benzoylamino)-4-(3-methoxy-phenyl)-butyryl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2-methyl-benzylamide [ No CAS ]
  • 5
  • [ 168899-58-9 ]
  • SM-322377 [ No CAS ]
  • 6
  • [ 168899-58-9 ]
  • (R)-3-[(2S,3S)-2-Hydroxy-3-(3-hydroxy-2-methyl-benzoylamino)-4-(4-methoxy-phenyl)-butyryl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,6-dimethyl-benzylamide [ No CAS ]
  • 7
  • [ 168899-58-9 ]
  • (R)-3-[(2S,3S)-4-Benzo[1,3]dioxol-5-yl-2-hydroxy-3-(3-hydroxy-2-methyl-benzoylamino)-butyryl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,6-dimethyl-benzylamide [ No CAS ]
  • 8
  • [ 168899-58-9 ]
  • [ 159989-64-7 ]
  • 9
  • [ 168899-58-9 ]
  • [ 767341-27-5 ]
  • 10
  • [ 168899-58-9 ]
  • acetic acid 3-[<i>N</i>'-(3-amino-2-isobutoxycarbonyloxy-4-phenyl-butyryl)-<i>N</i>'-benzyl-hydrazinocarbonyl]-2-methyl-phenyl ester [ No CAS ]
  • 11
  • [ 168899-58-9 ]
  • acetic acid 3-[<i>N</i>'-(3-amino-2-isobutoxycarbonyloxy-4-phenyl-butyryl)-<i>N</i>'-benzyl-hydrazinocarbonyl]-2-methyl-phenyl ester [ No CAS ]
  • 14
  • [ 168899-58-9 ]
  • KNI-1277 [ No CAS ]
  • 15
  • [ 168899-58-9 ]
  • KNI-1279 [ No CAS ]
  • 16
  • [ 168899-58-9 ]
  • [ 521275-20-7 ]
  • 17
  • [ 168899-58-9 ]
  • acetic acid 3-[<i>N</i>'-benzyl-<i>N</i>'-(3-<i>tert</i>-butoxycarbonylamino-2-isobutoxycarbonyloxy-4-phenyl-butyryl)-hydrazinocarbonyl]-2-methyl-phenyl ester [ No CAS ]
  • 18
  • [ 168899-58-9 ]
  • KNI-1166 [ No CAS ]
  • 19
  • [ 168899-58-9 ]
  • acetic acid 3-{<i>N</i>'-[3-(2-amino-3-methylsulfanyl-propionylamino)-2-isobutoxycarbonyloxy-4-phenyl-butyryl]-<i>N</i>'-benzyl-hydrazinocarbonyl}-2-methyl-phenyl ester [ No CAS ]
  • 20
  • [ 168899-58-9 ]
  • acetic acid 3-(<i>N</i>'-benzyl-<i>N</i>'-{3-[2-(2,6-dimethyl-phenoxy)-acetylamino]-2-isobutoxycarbonyloxy-4-phenyl-butyryl}-hydrazinocarbonyl)-2-methyl-phenyl ester [ No CAS ]
  • 21
  • [ 168899-58-9 ]
  • [4-({1-benzyl-3-[<i>N</i>-benzyl-<i>N</i>'-(3-hydroxy-2-methyl-benzoyl)-hydrazino]-2-hydroxy-3-oxo-propylcarbamoyl}-methoxy)-3,5-dimethyl-phenyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 22
  • [ 168899-58-9 ]
  • acetic acid 3-{3-[<i>N</i>'-(3-acetoxy-2-methyl-benzoyl)-<i>N</i>-benzyl-hydrazino]-1-benzyl-2-isobutoxycarbonyloxy-3-oxo-propylcarbamoyl}-2-methyl-phenyl ester [ No CAS ]
  • 23
  • [ 168899-58-9 ]
  • acetic acid 3-{3-[<i>N</i>'-(3-acetoxy-2-methyl-benzoyl)-<i>N</i>-benzyl-hydrazino]-1-benzyl-2-isobutoxycarbonyloxy-3-oxo-propylcarbamoyl}-2-methyl-phenyl ester [ No CAS ]
  • 24
  • [ 603-80-5 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • [ 168899-58-9 ]
YieldReaction ConditionsOperation in experiment
87.6% sulfuric acid; at 20 - 44℃; for 2h; Acetic acid (8750 mL), 3-hydroxy-2-methylbenzoic acid (3500 g), and sulfuric acid (70 mL) were charged into a 22 liter reactor. The reactor contents were stirred to give a homogeneous mixture. The mixture exothermed to 36 C. Acetic anhydride (2390 mL) was added to the mixture in the 22 L reactor. An exotherm warmed the reactor contents from 36 to 44 C. The reaction mixture was stirred at ambient temperature for two hours (reactor contents allowed to cool slowly). The reaction was tested for complete conversion of the starting material by TLC. The reaction mixture was generally a tan slurry at the completion of the reaction. Purified water (17500 mL) was added to a 50 L extractor, and the reaction mixture from the 22 L reactor was added to this water. The 22 L reactor was rinsed into the 50 L extractor with purified water (3500 mL). The reaction mixture was vacuum filtered, washing the reactor and filter cake with purified water (3500 mL). The wet filter cake was transferred to a 50 L extractor, and purified water (14000 mL) was added, with stirring, to obtain a homogeneous slurry. The reslurried mixture was vacuum filtered, and the reactor and filter cake were rinsed with purified water (3500 mL). The filter cake was pulled as dry as possible and then transferred to drying pans. The product was dried in a vacuum oven at 60 - 80 C and ≥28 mm Hg for 12 - 72 hours. Theoretical yield: 4466 g. Actual weight produced: 3910 g (87.6%). HPLC assay: 89.4% or 87.7%. Purification was achieved as follows. The crude 3-acetoxy-2-methylbenzoic acid (3910 g from above) and ethyl acetate (16.0 L) were charged to a 50 L reactor. The reactor contents were heated to reflux (77 C) until all solids went into solution. The reactor contents were cooled to < 70 C. Hexanes (19.5 L) were added to the reactor. The reactor contents were again heated to reflux (69 C), and then the mixture was cooled to <10 C for 1 hour. The cooled slurry from this step was vacuum filtered, and the reactor was rinsed with cold mother liquors. The filter cake was pulled as dry as possible and then transferred to drying pans. The product was dried in a vacuum oven at 60 - 70 C and ≥28 mm Hg for 12 - 72 hours. Theoretical yield: 3910 g. Actual weight produced: 3128 g (80%). This procedure improves the HPLC UV apparent purity from 89 - 92% to >98%. The single largest impurity drops from 4 - 6% to <1%. The isolated product is a tan solid. 1H NMR δ 8.0 (d, 1H), 7.3 (overlapping m, 2H), 2.5 (s, 3H), 2.3 (s, 3H).
  • 25
  • [ 603-80-5 ]
  • [ 168899-58-9 ]
YieldReaction ConditionsOperation in experiment
90.0% With hydrogenchloride; sodium hydroxide; In water; acetic anhydride; 3-Acetoxy-2-methylbenzoic acid 60.9 g (0.40 mol) of 3-hydroxy-2-methylbenzoic acid are introduced into 500 ml of 2N sodium hydroxide solution (1.00 mol) with stirring and the solution formed in the course of this is cooled to 5 C. 61.3 g (0.60 mol) of acetic anhydride are added to the cooled solution. The reaction mixture is cooled here such that the temperature does not exceed 8 C. The reaction mixture is then acidified with 88 ml of 37% hydrochloric acid. The precipitated product is filtered off, washed three times with 50 ml of water and dried in vacuo. 69.9 g of 3-acetoxy-2-methylbenzoic acid are obtained. This corresponds to a yield of 90.0% of theory. Melting point 147-148 C.
31% With sulfuric acid; acetic anhydride; In water; EXAMPLE 81 3-(Acetyl)hydroxy-2-methylbenzoic acid To a heterogeneous solution of 3.06 g (30 mmol) of acetic anhydride and 1.53 g (10 mmol) of 3-hydroxy-2-methylbenzoic acid was added one drop of concentrated sulfuric acid. The mixture was heated with a heat gun for 2 min. and then poured into 14 mL of cold water. The resulting precipitate was collected by vacuum filtration, washed twice with water and dried overnight in a vacuum oven. Recrystallization from 20% ethyl acetate/hexane (7 mL) gave 595 mg of a white solid, which is 3-(Acetyl)hydroxy-2-methyl benzoic acid. Yield: 31% IR (CHCl3): 3700-2300 (br), 1765, 1698, 1460, 1404, 1372, 1299, 1273, 1172, 1081, 1041, 1012, 933, 913, 865, 823 cm-1. MS (FD): m/e 194 (M+, 100).
31% With sulfuric acid; acetic anhydride; In water; EXAMPLE 81 3-(Acetyl)hydroxy-2-methylbenzoic acid STR69 To a heterogeneous solution of 3.06 g (30 mmol) of acetic anhydride and 1.53 g (10 mmol) of 3-hydroxy-2-methylbenzoic acid was added one drop of concentrated sulfuric acid. The mixture was heated with a heat gun for 2 min. and then poured into 14 mL of cold water. The resulting precipitate was collected by vacuum filtration, washed twice with water and dried overnight in a vacuum oven. Recrystallization from 20% ethyl acetate/hexane (7 mL) gave 595 mg of a white solid, which is 3-(Acetyl)hydroxy-2-methyl benzoic acid. Yield: 31% IR (CHCl3): 3700-2300 (br), 1765, 1698, 1460, 1404, 1372, 1299, 1273, 1172, 1081, 1041, 1012, 933, 913, 865, 823 cm-1. MS (FD): m/e 194 (M+, 100).
31% With sulfuric acid; acetic anhydride; In water; EXAMPLE 81 3-(Acetyl)hydroxy-2-methylbenzoic acid STR71 To a heterogeneous solution of 3.06 g (30 mmol) of acetic anhydride and 1.53 g (10 mmol) of 3-hydroxy-2-methylbenzoic acid was added one drop of concentrated sulfuric acid. The mixture was heated with a heat gun for 2 min. and then poured into 14 mL of cold water. The resulting precipitate was collected by vacuum filtration, washed twice with water and dried overnight in a vacuum oven. Recrystallization from 20% ethyl acetate/hexane (7 mL) gave 595 mg of a white solid, which is 3-(Acetyl)hydroxy-2-methyl benzoic acid. Yield: 31% IR (CHCl3): 3700-2300 (br), 1765, 1698, 1460, 1404, 1372, 1299, 1273, 1172, 1081, 1041, 1012, 933, 913, 865, 823 cm-1. MS (FD): m/e 194 (M+, 100).

  • 26
  • active charcoal [ No CAS ]
  • [ 1975-50-4 ]
  • [ 168899-58-9 ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydroxide; sulfuric acid; acetic anhydride; magnesium sulfate; sodium nitrite;palladium-carbon; In pyridine; ethanol; ethyl acetate; toluene; REFERENCE EXAMPLE 1 3-Acetoxy-2-methyl benzoic acid 3-Nitro-2-methyl benzoic acid (90.5 g, 0.500 mol) was dissolved in 1.0 mol/L aqueous solution (500 ml) of sodium hydroxide. 10% Palladium-carbon (4.5 g) was added and the mixture was stirred under a hydrogen atmosphere (2-3 atm) for 9 hours at 40 C. The catalyst was filtered off and conc. sulfuric acid (94.0 ml) was added under ice-cooling. An aqueous solution of sodium nitrite (35.0 g, 0.500 mol/150 ml) was added over one hour while stirring the mixture at riot more than 6 C., and after the dropwise addition, the mixture was heated at 65 C. for 1.5 hours. The inner temperature rose to 57 C. in an hour. The reaction mixture was cooled to room temperature, and saturated brine (300 ml) was added. The mixture was extracted with ethyl acetate (700 ml). The organic layer was washed with saturated brine (200 ml) and dried over magnesium sulfate. The solvent was distilled away to give 3-hydroxy-2-methyl benzoic acid as a pale brown solid. This substance was dissolved in pyridine (500 ml), and acetic anhydride (100 ml) was added at room temperature, which was followed by stirring at room temperature for 3.5 hours. Ethanol (100 ml) which was kept at not more than 10 C. was added to the reaction mixture, and the mixture was stirred for another hour at room temperature. The mixture was concentrated to give a brown oil. The oil was dissolved in ethyl acetate (800 ml) and washed successively with 1N hydrochloric acid (500 ml) and saturated brine (300 ml). Magnesium sulfate and active charcoal (4.00 g) were added to the organic layer, and the mixture was stirred for 30 minutes. The insoluble matter was filtered off and the filtrate was concentrated to dryness. Acetic acid in this product was removed by azeotropy using toluene (400 ml), and the residue was washed with toluene (450 ml) to give 3-acetoxy-2-methyl benzoic acid (70.1 g, yield 72%) as colorless crystals, melting point 146-148 C. 1 H-NMR (CDCl3, 300 MHz) δ: 7.95 (dd,1H,J=1.5,7.3Hz), 7.30 (t,1H, J=7.7Hz), 7.24 (dd,1H,J=1.5,8.1Hz), 2.46 (s,3H), 2.36 (s,3H) IR (KBr): 2984, 2816, 1766, 1687, 1460, 1311, 1279, 1211, 1039, 930, 766, 752 cm-1 Elemental Analysis (C10 H10 O4) Calculated: C,61.85;H,5.19. Found: C,61.91;H,4.94.
  • 27
  • trisodium 1,3,5-naphthalenetrisulfonate [ No CAS ]
  • [ 108-24-7 ]
  • [ 168899-58-9 ]
YieldReaction ConditionsOperation in experiment
71% In einem Nickelautoklaven werden in ein Gemisch aus 356,0 g wässriger Natronlauge (45 %ig); 126,0 g Natriumhydroxid-Pastillen und 127,0 g Calciumhydroxid 300,0 g Trinatrium-1,3,5-naphthalintrisulfonat (70,9 %ig, berechnet als freie Säure) so eingerührt, dass eine gut rührbare, breiartige Suspension entsteht. Der Autoklav wird verschlossen und auf 310C aufgeheizt. Der Innendruck (Eigendruck) steigt dabei auf 50 bar. Es wird 5 Stunden bei der Reaktionstemperatur nachgerührt und danach auf 90C abgekühlt. Bei dieser Temperatur werden 200,0 g Wasser eingepumpt und danach auf Raumtemperatur abgekühlt. Die erhaltene Suspension wird abgesaugt und mit 609,6 g Wasser nachgewaschen. Man erhält 295,0 g eines bräunlich-weißen, feinteiligen Feststoffs und 1388,8 g einer dunkelbraunen Lösung. In einem Kolben werden 300,0 g der Lösung aus Beispiel 3 vorgelegt. Man gibt 5 g Aktivkohle zu und stellt durch Zudosieren von Salzsäure (37 %ig) einen pH-Wert von 7,0 ein, erhitzt zum Rückfluss, klärt die Reaktionslösung und wäscht mit Wasser nach. Die geklärte Reaktionslösung wird in den Kolben zurückgegeben, auf 0C abgekühlt und durch Zudosieren von Natronlauge (30 %ig) ein pH von 9,6 eingestellt. Jetzt werden bei 0 bis 5C Acetanhydrid und Natronlauge simultan so eindosiert, dass der pH-Wert im Bereich von 9,3 bis 9,7 bleibt. Es werden in 1 Stunde 14,8 g Acetanhydrid und 22,3 g Natronlauge (30 %ig) zudosiert. Danach wird 0,5 Stunde bei der gleichen Temperatur nachgerührt. Danach wird bei 5C durch Zugabe von Salzsäure ein pH-Wert von 1 eingestellt. Dabei fällt das Produkt als weißer Niederschlag aus. Das Produkt wird auf einer Glasfiltemutsche abgesaugt und mit Wasser nachgewaschen. Der Niederschlag wird im Vakuumtrockenschrank getrocknet. Man erhält 17,4 g 3-Acetoxy-2-methylbenzoesäure (Gehalt 98,2 %). Das entspricht einer isolierten Ausbeute bezogen auf Trinatrium-1,3,5-naphthalintrisulfonat von 71 %d.Th.
67% In einem Nickelautoklaven werden in ein Gemisch aus 232,0 g wässriger Natronlauge (45 %ig) und 194,0 g Natriumhydroxid 300,0 g Trinatrium-1,3,5-naphthalintrisulfonat (70,9 %ig, berechnet als freie Säure) so eingerührt, dass eine gut rührbare, breiartige Suspension entsteht. Der Autoklav wird verschlossen und auf 280C aufgeheizt. Der Innendruck (Eigendruck) steigt dabei auf 18,4 bar. Es wird 6 Stunden bei Reaktionstemperatur nachgerührt und danach auf 90C abgekühlt. Bei dieser Temperatur werden 200,0 g Wasser eingepumpt und danach auf Raumtemperatur abgekühlt. Die erhaltene Suspension wird abgesaugt und mit 187,3 g Wasser nachgewaschen. Man erhält 251,8 g eines bräunlich-weißen, feinteiligen Feststoffs und 795,7 g einer dunkelbraunen Lösung. In einem Kolben werden 390,0 g der Lösung aus Beispiel 1 vorgelegt. Man gibt 20,0 g Aktivkohle zu und stellt durch Zudosieren von Salzsäure (37 %ig) einen pH-Wert von 7,0 ein, erhitzt zum Rückfluss, klärt die Reaktionslösung und wäscht mit Wasser nach. Die geklärte Reaktionslösung wird in den Kolben zurückgegeben, auf 0C abgekühlt und durch Zudosieren von Natronlauge (30 %ig) ein pH von 9,6 eingestellt. Jetzt werden bei 0 bis 5C Acetanhydrid und Natronlauge simultan so eindosiert, dass der pH-Wert im Bereich von 9,3 bis 9,7 bleibt. Es werden in 1 Stunde 39,8 g Acetanhydrid und 75,9 g Natronlauge (30 %ig) zudosiert. Danach wird 0,5 Stunde bei der gleichen Temperatur nachgerührt. Danach wird bei 5C durch Zugabe von Salzsäure ein pH-Wert von 1 eingestellt. Dabei fällt das Produkt als weißer Niederschlag aus. Das Produkt wird auf einer Glasfilternutsche abgesaugt und mit Wasser nachgewaschen. Der Niederschlag wird im Vakuumtrockenschrank getrocknet. Man erhält 38,7 g 3-Acetoxy-2-methylbenzoesäure (Gehalt 95,0 %). Das entspricht einer isolierten Ausbeute bezogen auf Trinatrium-1,3,5-naphthalintrisulfonat von 67 % d.Th.
  • 28
  • C25H33N3O3S*(x)ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C35H41N3O6S [ No CAS ]
  • 29
  • C24H30ClN3O3S*(x)ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C34H38ClN3O6S [ No CAS ]
  • 30
  • C23H27Cl2N3O3S*ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C33H35Cl2N3O6S [ No CAS ]
  • 31
  • C23H27ClFN3O3S*(x)ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C33H35ClFN3O6S [ No CAS ]
  • 32
  • C23H27F2N3O3S*(x)ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C33H35F2N3O6S [ No CAS ]
  • 33
  • C24H31N3O4S*(x)ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C34H39N3O7S [ No CAS ]
  • 34
  • C24H30FN3O3S*(x)ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C34H38FN3O6S [ No CAS ]
  • 35
  • C24H31N3O3S*(x)ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C34H39N3O6S [ No CAS ]
  • 36
  • C24H31N3O3S*(x)ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C34H39N3O6S [ No CAS ]
  • 37
  • C25H31N3O3S*(x)ClH [ No CAS ]
  • [ 168899-58-9 ]
  • C35H39N3O6S [ No CAS ]
 

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