2-(6-METHYL-1-BENZOFURAN-3-YL) ACETIC ACID synthesis

4synthesis methods

Product Name:2-(6-METHYL-1-BENZOFURAN-3-YL) ACETIC ACID
CAS Number:142917-39-3
Molecular formula:C11H10O3
Molecular Weight:190.2

2H-1-Benzopyran-2-one, 4-(bromomethyl)-7-methyl-

41321-75-9
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2-(6-METHYL-1-BENZOFURAN-3-YL) ACETIC ACID

142917-39-3
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Yield:142917-39-3 95%

Reaction Conditions:

with sodium hydroxide in water;Reflux;Perkin Coumarin Rearrangement;

Steps:

Synthesis of (5-Methyl-benzofuran-3-yl)-acetic Acid (5a)

General procedure: The substituted-4-bromomethylcoumarin 4 (10 mM) was refluxed in 1M NaOH (100 mL) for1-2 h (monitored by TLC). Th ereaction mixture was cooled and neutralized with 1M HCl ,and then the obtained product was filtered and dried. The obtained products were sufficiently pure and hence were not recrystallized. Mp 97-98 °C (literature mp 98-100 °C),^[15] yield 95%; IR (KBr, ν in cm^-1): 3439 (br, OH), 1722 (C=O); ¹H NMR (400 MHz, DMSO-d₆): δ 2.39 (s, 3H, C5-CH₃), 3.65 (s, 2H, C3-CH₂), 7.11 (d, J=8.4 Hz, 1H, C6-H), 7.37 (d, J=0.4 Hz, 1H, C4-H), 7.42 (d, J=8.4 Hz, 1H, C7-H), 7.83 (s, 1H, C2-H), 12.46 (s, 1H, COOH); ¹³C NMR (400 MHz, DMSO-d₆): 20.88, 28.95, 110.74, 113.68, 119.71, 125.42, 127.81, 131.39, 143.44, 152.92, 171.92. LCMS m=z: 191 [M+1]. Anal. calcd. for C₁₁H₁₀O₃: C, 69.46; H, 5.30. Found: C, 69.38; H, 5.28.

References:

Basanagouda, Mahantesha;Narayanachar;Majati, Iranna B.;Mulimani, Shiddappa S.;Sunnal, Satish B.;Nadiger, Rohit V.;Ghanti, Ashok S.;Gudageri, Siddeshwar F.;Naik, Ravi;Nayak, Akshata [Synthetic Communications,2015,vol. 45,# 19,p. 2195 - 2202] Location in patent:supporting information

Ethyl 2-(6-methylbenzofuran-3-yl)acetate

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142917-39-3
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References

20895-41-4
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142917-39-3
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108-39-4
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142917-39-3
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