5-Chloro-2,3-dimethoxybenzaldehyde → 1-(5-Chloro-2,3-dimethoxyphenyl)ethanol

Temperature

0 °C

To a stirred solution of 5-chloro-2,3-dimethoxy-benzaldehyde (7.0 g, 34.90 mmol) in dry diethyl ether (500 mL) at 0° C. was added methylmagnesium bromide of 3.0 M in diethyl ether (29 mL, 87.22 mmol). The reaction mixture was brought to room temperature and stirred for 30 min; refluxed for 3 h; then cooled to 0° C. and quenched by adding saturated aqueous NH4Cl. The two liquid layers were separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water, dried, and concentrated to the crude compound which was purified by silica gel column (10-25% ethyl acetate in hexanes) to afford 1-(5-chloro-2,3-dimethoxy-phenyl)-ethanol (5.67 g, 75%): 1H NMR (400 MHz, CDCl3): δ 7.00 (d, 1H), 6.81 (d, 1H), 5.11 (m, 1H), 3.86 (s, 6H), 2.30 (d, 1H), 1.48 (d, 3H).

1. customwas brought to room temperature
2. temperaturerefluxed for 3 h
3. customquenched
4. additionby adding saturated aqueous NH4Cl
5. customThe two liquid layers were separated
6. extractionThe aqueous layer was extracted with diethyl ether
7. washThe combined organic layers were washed with water
8. customdried
9. concentrationconcentrated to the crude compound which
10. customwas purified by silica gel column (10-25% ethyl acetate in hexanes)

ORD record

ord-7a1a98b2b4334265be402c99c68aeb87

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968538B2