3-Methyl-benzo[b]thiophen-5-ol synthesis

3synthesis methods

Product Name:3-Methyl-benzo[b]thiophen-5-ol
CAS Number:3610-07-9
Molecular formula:C9H8OS
Molecular Weight:164.22

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Yield:-

Reaction Conditions:

with pyridine hydrochloride at 190; for 3 h;Inert atmosphere;

Steps:

41.A

METHOD A. 3-METHYL-5-HYDROXYBENZOTHIOPHENEA mixture of the 3-methyl-5-methoxybenzothiophene (6.5 g, 36.1 mmol), generated in Preparative Example 29, Method A, and pyridine-HCl (10.5 g, 90.25 mmol) was heated to 190° C. under N₂for 3 h. The reaction was monitored by examining worked-up aliquots of the reaction mixture by thin-layer chromatography (TLC) with 20% EtOAc/hexane as eluant. The reaction was cooled in an ice bath and ice-H₂O was added. The resulting mixture was extracted with EtOAc. The organic extract was washed with 2 N HCl and brine, dried over MgSO₄, filtered, and the filtrate concentrated in vacuo. The resulting residue was purified by silica gel chromatography with 20% EtOAc/hexane as the eluant to afford the desired product.¹H NMR (500 MHz, CDCl₃) δ (ppm): 7.60 (d, 1H), 7.12 (s, 1H), 7.10 (d, 1H), 6.85 (dd, 1H), 2.35 (s, 3H).

References:

US2010/279983,2010,A1 Location in patent:Page/Page column 23-24

19404-18-3
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References

5-hydroxy-3-methylbenzo[b]thiophene-2-carboxylic acid

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3610-07-9
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References