ChemicalBook CAS DataBase List Methyl 2-Chloro-5-methoxybenzoate

Methyl 2-Chloro-5-methoxybenzoate synthesis

6synthesis methods

Product Name:Methyl 2-Chloro-5-methoxybenzoate
CAS Number:54810-63-8
Molecular formula:C9H9ClO3
Molecular Weight:200.62

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54810-63-8
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$26.00/100mg

Yield: 94%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 40; for 21 h;

Steps:

1.1
Methyl iodide (1.6 mL, 26 mmol) was added to a stirred suspension of 2-chloro-5- hydroxybenzoic acid 10 (0.80 g, 4.6 mmol) and K₂CO₃ (2.85 g, 20 mmol) in DMF (40 mL). The reaction mixture was heated at 40 ⁰C for 5 h, followed by another addition of methyl iodide (1.2 mL, 19 mmol). After 16 h of stirring at 40 ⁰C, the reaction mixture was cooled to room temperature and H₂O (100 mL) was added, followed by extraction with Et₂O (2 x 60 mL, 1 x 30 mL). The organic layers were washed sequentially with aq. NaOH (0.1 M, 100 mL) and H₂O (2 x 80 mL), dried (Na₂SO-O, and concentrated- under reduced pressure to give the benzoate 11 (0.81 g, 94 %) as a yellow oil; ¹H NMR (200 MHz, DMSO-d₆) δ 7.49 (I H, d, J = 8.9 Hz, 3-CH), 7.32 (IH, d, J= 3.1 Hz, 6-CH), 7.16 (1 H, dd, J= 8.9, 3.1 Hz, 4-CH), 3.86 (3 H, s, CH₃), 3.81 (3H₁ S₅ CH₃).