ChemicalBook CAS DataBase List 2,3-DIHYDRO-1,4-BENZODIOXIN-5-YLMETHANOL

2,3-DIHYDRO-1,4-BENZODIOXIN-5-YLMETHANOL synthesis

5synthesis methods

Product Name:2,3-DIHYDRO-1,4-BENZODIOXIN-5-YLMETHANOL
CAS Number:274910-19-9
Molecular formula:C9H10O3
Molecular Weight:166.17

2,3-Dihydro-1,4-benzodioxine-5-carboxylic acid

4442-53-9

2,3-DIHYDRO-1,4-BENZODIOXIN-5-YLMETHANOL

274910-19-9

2,3-Dihydro-1,4-benzodiene-5-carboxylic acid (5.00 g, 28.0 mmol) was dissolved in tetrahydrofuran (150 mL) at 0 °C and lithium aluminum hydride (2.13 g, 56.0 mmol) was added slowly. The reaction mixture was stirred at 0 °C for 10 min, then brought to room temperature and continued stirring for 18 h. The reaction was completed by the addition of water (2.13 g, 56.0 mmol). Upon completion of the reaction, the reaction was quenched by the addition of water (150 mL) and subsequently extracted with ethyl acetate (2 x 100 mL). The organic phases were combined, washed with saturated saline (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product (2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methanol as a yellow oil (3.22 g, 99% yield). The product was characterized by 1H NMR (CDCl3): δ 6.87-6.79 (m, 3H), 4.66 (s, 2H), 4.32-4.30 (m, 2H), 4.28-4.25 (m, 2H), 2.19 (bs, 1H). The [M+H-18]+ peak was detected by mass spectrometry, m/z = 149.5.

4442-53-9 Synthesis

4442-53-9
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274910-19-9
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$29.00/100mg

Yield:274910-19-9 99%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 18 h;

Steps:

(2,3-Dihydrobenzo[Z>] [l,4]dioxin-5-yl)methanol (20)

To a solution of 2,3-dihydrobenzo[￡][l,4]dioxine-5-carboxylic acid (5.00 g, 28.0 mmol) in THF (150 mL) at 0 °C was added lithium aluminium hydride (2.13 g, 56.0 mmol) in small portions. The reaction mixture was stirred at 0 °C for 10 min and stirred for a further 18 h at r.t. Water (150 mL) was added to the reaction mixture which was extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over Na₂S0₄, filtered and concentrated under reduced pressure to obtain 20 as yellow oil (3.22 g, 99%). 1H NMR (CDC1₃) δ 6.87-6.79 (m, 3H), 4.66 (s, 2H), 4.32-4.30 (m, 2H), 4.28-4.25 (m, 2H), 2.19 (bs, 1H). Found: [M+H-18]=149.5

References:

WO2017/155909,2017,A1 Location in patent:Paragraph 0075