ChemicalBook CAS DataBase List (2,3-dihydrobenzofuran-6-yl)methanol

(2,3-dihydrobenzofuran-6-yl)methanol synthesis

8synthesis methods

Product Name:(2,3-dihydrobenzofuran-6-yl)methanol
CAS Number:1083168-69-7
Molecular formula:C9H10O2
Molecular Weight:150.17

Methyl 2,3-dihydrobenzofuran-6-carboxylate

1083168-68-6
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1083168-69-7
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Yield:1083168-69-7 92%

Reaction Conditions:

Stage #1: methyl 2,3-dihydrobenzofuran-6-carboxylatewith lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 1 h;
Stage #2: with sodium hydroxide;water in tetrahydrofuran;

Steps:

G.f

Stepf: (2,3-Dihydrobenzofuran-6-yl)methanol; To a stirred solution of lithium aluminium hydride (6.1 g, 250 mmol) in THF(300 mL) was added a solution of methyl 2,3-dihydrobenzofuran-6-carboxylate (17.8 g, 100 mmol) in THF at 0^°C. The mixture was stirred at room temperature for 1 h. A saturated aqueous NaOH solution was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over Na₂SO₄, filtered and concentrated to afford (2,3-dihydrobenzofuran-6-yl)methanol (13.8 g, 92.0% yield). ¹H NMR (400 MHz, CDCl₃) δ: 7.17 (d, J= 7.2, IH), 6.84 (d, J= 7.2, IH), 6.81 (s, IH), 4.62 (s, 2H), 4.58 (t, J= 8.4, 2H), 3.20 (t, J= 8.4, 2H),) 1.67 (br s, IH).

References:

WO2008/141119,2008,A2 Location in patent:Page/Page column 77; 79

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