1,2-Dichloroethane → HCID 11708318, compound

Temperature

67.5 °C

A mixture of 3-hydroxy-4-methoxybenzaldehyde (14) (10.0 g, 65.7 mmol), K2CO3 (45.4 g, 329 mmol), 1,2-dichloroethane (104 mL, 1.31 mol), and DMF (300 mL) was stirred at 65-70° C. for 16 h. After cooling, 1,2-dichloroethane was removed under reduced pressure, the remaining slurry was poured onto ice and the mixture was extracted with Et2O (3×250 mL) and EtOAc (4×250 mL). The combined organic layers were washed with water (4×400 mL) and brine (2×400 mL), dried (MgSO4), and the solvent was removed in vacuo. Crystallization from EtOAc/hexane provided 15 (11.9 g, 84%) as colorless needles. 1H NMR (200 MHz, CDCl3): δ=3.88 (t, J=6.1 Hz, 2 H, 2′-H2), 3.97 (s, 3 H, OMe), 4.35 (t, J=6.1 Hz, 2 H, 1′-H2), 7.01 (d, J=8.1 Hz, 1 H, 5-H), 7.43 (d, J=1.8 Hz, 1 H, 2-H), 7.51 (dd, J=8.1, 1.8 Hz, 1 H, 6-H), 9.86 (s, 1 H, CHO) ppm; 13C NMR (50.3 MHz, CDCl3): δ=41.5 (C-2′), 56.2 (OMe), 68.9 (C-1′), 111.0, 111.3 (C-2, C-5), 127.4 (C-6), 129.9 (C-1), 148.1 (C-3), 154.9 (C-4), 190.7 (CHO) ppm; MS (70 eV, EI): m/z (%)=214 (100) [M]+, 151 (57) [M-CH2)2Cl]+; C10H11ClO3 (214.65): calcd. C, 55.96; H, 5.17; found C, 56.04; H, 4.97.

1. temperatureAfter cooling
2. custom1,2-dichloroethane was removed under reduced pressure
3. additionthe remaining slurry was poured onto ice
4. extractionthe mixture was extracted with Et2O (3×250 mL) and EtOAc (4×250 mL)
5. washThe combined organic layers were washed with water (4×400 mL) and brine (2×400 mL)
6. dry with materialdried (MgSO4)
7. customthe solvent was removed in vacuo
8. customCrystallization from EtOAc/hexane

ORD record

ord-29219471893042768a9102ca6e6a4a22

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940784B2