2-(3-(methoxycarbonyl)phenyl)acetic acid synthesis
- Product Name:2-(3-(methoxycarbonyl)phenyl)acetic acid
- CAS Number:52787-19-6
- Molecular formula:C10H10O4
- Molecular Weight:194.18
52787-20-9
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52787-19-6
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Yield: 90%
Reaction Conditions:
Stage #1:3-methoxycarbonylphenylacetic acid methyl ester with potassium carbonate in methanol;water at 20; for 12 h;
Stage #2: with hydrogenchloride in water
Steps:
14 2- (3- (methoxycarbonyl)phenyl) acetic acid (77)
A solution of K2C03 (700 mg, 5.07 mmol) in H20 (10 mL) was added to a solution of methyl 3- (2-methoxy-2-oxoethyl) benzoate 76, (500 mg, 2.40 mmol) in methanol (10 mL) and stirred overnight at room temperature. Reaction mixture was concentrated and dissolved in water (20 mL) . Aqueous later was extracted with EtOAc to the unreacted diester 76, acidified with IN HC1, and extracted with EtOAc (30 mL x 2) . Organic layer was dried (anhydrous sodium sulfate) and concentrated in vacuo. The crude product was chromatographed on silica gel (Hexanes/EtOAc, 5:1) to yield target compound 77. Yield 508 mg, 90%. Rf = 0.36, H 1H NMR (400 MHz, Methanol-d4) δ 7.97 (d, J = 1.7 Hz, 1H) , 7.91 (dt, J = 7.8, 1.4 Hz, 1H) , 7.57 - 7.49 (m, 1H) , 7.43 (t, J = 7.6 Hz, 1H) , 3.91 (s, 3H) , 3.67 (s, 2H) ; [M+H]+ = 195.14 (APCI+) .
References:
Location in patent:Page/Page column 63; 65
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1000210-73-0
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52787-19-6
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52787-19-6
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