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.
