| Identification | More | [Name]
3-Methoxybenzyl chloride | [CAS]
824-98-6 | [Synonyms]
1-CHLOROMETHYL-3-METHOXYBENZENE
3-CHLOROMETHYLANISOLE
3-METHOXYBENZYL CHLORIDE
AKOS BBS-00003862
M-METHOXYBENZYL CHLORIDE
1-(chloromethyl)-3-methoxy-benzen
Anisole, m-(chloromethyl)-
Benzene, 1-(chloromethyl)-3-methoxy-
m-(Chloromethyl)anisole
Toluene, alpha-chloro-m-methocy-
alpha-Chloro-3-methoxytoluene
3-Methoxybenzalchloride
META-(CHLOROMETHYL)ANISOL
3-METHOXYBENZYL CHLORIDE/3-(CHLOROMETHYL)ANISOLE
3-METHOXYBENZYL CHLORIDE, 98+%
(3-Methoxyphenyl)methyl chloride
a-Chloro-m-methoxytoluene
1-Methoxy-3-(chloromethyl)benzene
3-Methoxy-1-(chloromethyl)benzene | [EINECS(EC#)]
212-541-1 | [Molecular Formula]
C8H9ClO | [MDL Number]
MFCD00000907 | [Molecular Weight]
156.61 | [MOL File]
824-98-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to light yellow liquid | [Melting point ]
101.67°C | [Boiling point ]
124 °C13 mm Hg(lit.) | [density ]
1.078 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.544(lit.)
| [Fp ]
215 °F
| [storage temp. ]
Store at?0-5°C | [solubility ]
Chloroform, Methanol (Slightly) | [form ]
clear liquid | [color ]
Colorless to Light yellow | [Specific Gravity]
1.157 (20/4℃) | [Sensitive ]
Moisture Sensitive | [BRN ]
636684 | [InChIKey]
VGISFWWEOGVMED-UHFFFAOYSA-N | [CAS DataBase Reference]
824-98-6(CAS DataBase Reference) | [NIST Chemistry Reference]
«alpha»-Chloro-3-methoxytoluene(824-98-6) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
1
| [F ]
19-21 | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29093090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to light yellow liquid | [Uses]
3-Methoxybenzyl chloride was used to alkylate 8-benzyloxy-2(1H)-quinolinone in the presence of DMF and NaH. It was also used in the synthesis of diarylmethanes via in situ organozinc-mediated, palladium-catalyzed cross-coupling between benzyl and aryl halide. | [Application]
3-Methoxybenzyl chloride is used for protection of alcohols, thiols, phenols, amides, amines, and carboxylic acids. | [Synthesis]
General procedure for the synthesis of 3-methoxybenzyl chloride from m-methoxybenzyl alcohol: 3-methoxybenzyl alcohol (248 μL, 2.0 mmol) and triethylamine (335 μL, 2.4 mmol) were dissolved in dichloromethane (DCM, 7 mL). Thionyl chloride (218 μL, 3.0 mmol) was added slowly. The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was washed with 1N HCl aqueous solution. The organic phase was dried with anhydrous magnesium sulfate (MgSO?). The solvent was removed under reduced pressure to give the target product 3-methoxybenzyl chloride (313 mg, 100%) as a yellow oil.
Next, 4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylic acid (Example 74, 85 mg, 0.26 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF, 1 mL), followed by addition of cesium carbonate (169 mg, 0.52 mmol) and 3-methoxybenzyl chloride ( 81 mg, 0.52 mmol). The reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (EtOAc) and water. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine and dried with anhydrous magnesium sulfate (MgSO?). The solvent was removed under reduced pressure. The crude product was purified by fast chromatography using a mixture of cyclohexane/ethyl acetate (8:2) as eluent to afford the target product (3-methoxyphenyl)methyl 4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylate as a pale yellow oil (11 mg, 9%).
Product characterization data: 1H NMR (300 MHz, CDCl?) δ 2.62 (s, 3H), 2.71 (dd, J = 15.8, 2.2 Hz, 1H), 2.92 (dd, J = 15.8, 7.5 Hz, 1H), 3.31 (s, 3H), 3.37 (ddt, J = 10.0, 8.5, 3.6 Hz, 1H). 3.46 (dt, J = 10.0, 4.1 Hz, 1H), 3.70-3.79 (m, 4H), 4.13-4.23 (m, 2H), 5.04 (d, J = 12.7 Hz, 1H), 5.11 (d, J = 12.7 Hz, 1H), 6.64 (s, 1H), 6.70 (d, J = 7.5 Hz, 1H), and 6.81 (dd, J = 8.2, 2.5 Hz, 1H), 7.10 (d, J = 8.4 Hz, 2H), 7.16-7.23 (m, 3H). Mass spectrum (MS): [M + H]? m/z 444. high-resolution mass spectrum (HRMS): calculated value of C??H??N?Cl, [M + H]? 444.1578, measured value 444.1579. | [storage]
3-Methoxybenzyl chloride is stored over K2CO3 to stabilize it. | [References]
[1] Patent: WO2016/16238, 2016, A1. Location in patent: Page/Page column 126-127
[2] Organic Process Research and Development, 2016, vol. 20, # 2, p. 568 - 573
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 19, p. 8889 - 8895
[4] Journal of Organic Chemistry, 1998, vol. 63, # 25, p. 9565 - 9568
[5] Australian Journal of Chemistry, 1992, vol. 45, # 1, p. 71 - 97 |
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