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| | METHYL 3-METHOXY-4-METHYLBENZOATE Basic information | | Preparation |
| | METHYL 3-METHOXY-4-METHYLBENZOATE Chemical Properties |
| Melting point | 50-54 °C (lit.) | | Boiling point | 119-120°C 1mm | | density | 1.075±0.06 g/cm3(Predicted) | | refractive index | 1.5295 | | Fp | >230 °F | | form | powder to crystal | | color | White to Almost white | | BRN | 1948339 | | InChI | InChI=1S/C10H12O3/c1-7-4-5-8(10(11)13-3)6-9(7)12-2/h4-6H,1-3H3 | | InChIKey | LLEXCSBUSVRBCA-UHFFFAOYSA-N | | SMILES | C(OC)(=O)C1=CC=C(C)C(OC)=C1 | | CAS DataBase Reference | 3556-83-0(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 1 | | HS Code | 29189900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | METHYL 3-METHOXY-4-METHYLBENZOATE Usage And Synthesis |
| Preparation | Methyl 3-methoxy-4-methylbenzoate is synthesized by the following steps:A mixture of methyl 3-hydroxy-4-methylbenzoate 36 (25 g, 0.151 mol), Me2SO4 (28.3 ml, 0.386 mol), anhydrous K2CO3 (103.5 g, 0.75 mol) was refluxed in acetone for 2 hours. K2CO3 was filtered off, washed thoroughly with acetone. The filtrates were combined and concentrated, the residue was redissolved in EtOAc washed with water, dried (anhydrous Na2SO4), filtered and concentrated in vacuo to furnish a white solid (19.52 g). Yield : 72%. | | Chemical Properties | White low melting solid | | Uses | Methyl 3-Methoxy-4-methylbenzoate has been used as a reactant in the preparation of an antimalaria drug that consists of the 4-aminoquinoline pharmacophore of chloroquine with clotrimazole-based antimalarials. | | Synthesis Reference(s) | Journal of Medicinal Chemistry, 33, p. 1771, 1990 DOI: 10.1021/jm00168a036 | | General Description | Methyl 3-methoxy-4-methylbenzoate can be prepared by reacting diazomethane with 3-methoxy-4-methylbenzoic acid in ether. | | Synthesis | Synthesis of methyl 3-methoxy-4-methylbenzoate: 3-hydroxy-4-methylbenzoic acid (15.2 g, 100 mmol) was suspended in 30 mL of water, and the pH was adjusted to 11.5 with 50% aqueous sodium hydroxide. dimethyl sulfate (15.8 mL, 167 mmol) was added slowly and dropwise over a period of 4 h at about 20 °C, while maintaining the pH of the reaction system between 11.2 and 11.8 by supplementing with sodium hydroxide solution. pH of the reaction system between 11.2 and 11.8. Subsequently, the reaction mixture was warmed up to 55 °C and the addition of dimethyl sulfate (6 mL, 63 mmol) was continued dropwise over a period of 4 hours while controlling the pH in the range of 8.2 to 9.0. Upon completion of the reaction, the organic phase was separated and purified by silica gel fast column chromatography (eluent: petroleum ether/ethyl acetate = 10/1, v/v) to afford the target product methyl 3-methoxy-4-methylbenzoate (11.8 g, 66% yield). The product was confirmed by 1H NMR (300 MHz, CDCl3): δ 7.55 (d, 2H, J=7.5 Hz), 7.48 (s, 1H), 7.18 (d, 1H, J=7.5 Hz), 3.91 (s, 3H), 3.89 (s, 3H), 2.26 (s, 3H); the LC-MS analysis showed m/z=181 (MH)+. | | References | [1] Patent: US2009/191183, 2009, A1. Location in patent: Page/Page column 51
[2] Canadian Journal of Chemistry, 1981, vol. 59, p. 2314 - 2327 |
| | METHYL 3-METHOXY-4-METHYLBENZOATE Preparation Products And Raw materials |
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