METHYL 3-CHLORO-4-HYDROXYBENZOATE synthesis
- Product Name:METHYL 3-CHLORO-4-HYDROXYBENZOATE
- CAS Number:3964-57-6
- Molecular formula:C8H7ClO3
- Molecular Weight:186.59
67-56-1
3964-58-7
3964-57-6
1. Sulfuric acid (3 mL, 56.3 mmol) was added to a solution of 3-chloro-4-hydroxybenzoic acid (1.0 g, 5.8 mmol) in methanol (30 mL). 2. The reaction mixture was stirred at 60 °C for 12 hours. 3. Upon completion of the reaction, the mixture was cooled to room temperature and the methanol was removed under vacuum. 4. The residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate (3 x 30 mL). 5. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford methyl 3-chloro-4-hydroxybenzoate (0.9 g, 83% yield) as a white solid. 6. The product was characterized by ESI-MS and NMR: ESI-MS m/z calculated 186.5, measured 187.5 (M + 1)+; retention time: 1.17 min (3 min run). ,2.2H, 1H), 7.06 (d, J = 8.8 Hz, 1H) and 3.90 (s, 3H).
67-56-1
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3964-58-7
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3964-57-6
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Yield:3964-57-6 83%
Reaction Conditions:
with sulfuric acid at 60; for 12 h;
Steps:
[00418] Preparation of 3-Chloro-4-isopropoxybenzoic acid[00419] Step 1:[00420] To a solution of 3-chloro-4-hydroxy-benzoic acid (1.0 g, 5.8 mmol) in methanol (30 mL) was added sulfuric acid (3 mL, 56.3 mmol) and the mixture was stirred at 60 °C for 12 hours. The reaction mixture was cooled to room temperature and the methanol was removed in vacuo. The residue was partitioned between a saturated solution of 2CO3 and ethyl acetate (3 x 30 mL), dried, filtered and concentrated in vacuo to yield methyl 3-chloro-4-hydroxy-benzoate (0.9 g, 83 %) as a white solid. ESI- MS m/z calc 186.5, found 187.5 (M+l)+; Retention time: 1.17 minutes (3 min run). NMR (400.0 MHz, CDC13) δ 8.05 (d, J = 2.2 Hz, 1H), 7.90 - 7.87 (dd, J= 8.8, 2.2 H, 1H), 7.06 (d, J = 8.8 Hz, 1H) and 3.90 (s, 3H).
References:
WO2012/125613,2012,A1 Location in patent:Page/Page column 145
99-76-3
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3964-57-6
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