Water → 5-Methoxy-2-(methoxymethoxy)benzaldehyde

To a solution of 2-hydroxy-5-methoxybenzaldehyde (10 g, 67.5 mmol) and diisopropylethylamine (14 mL, 80 mmol) in CH2Cl2 (100 mL) was added chloromethyl methyl ether (6.1 mL, 80 mmol) at 0° C., and the mixture was stirred for 15 hours at room temperature. Then, water was added to the solution, the aqueous layer was extracted with CH2Cl2 (100 mL×3). The combined organic layer was washed with saturated aqueous NaCl (100 mL×2), water (100 mL×1), dried over MgSO4, and evaporated to afford the objective compound as a brown oil (11.76 g, 91%), which was used for next reaction without further purification: 1H-NMR (400 MHz, CDCl3) δ3.52 (s, 3H), 3.81 (s, 3H), 5.24 (s, 2H), 7.12 (dd, 1H, J=9.6, 3.2 Hz), 7.18(d, 1H, J=9.6 Hz), 7.32(d, 1H, J=3.2 Hz), 10.47 (s, 1H).

1. extractionthe aqueous layer was extracted with CH2Cl2 (100 mL×3)
2. washThe combined organic layer was washed with saturated aqueous NaCl (100 mL×2), water (100 mL×1)
3. dry with materialdried over MgSO4
4. customevaporated

ORD record

ord-cdb9515288a24c75b77d8a436f7b376c

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262301B1