Hydrochloric Acid → 2,3-Dihydroxy-4-methoxybenzaldehyde

An anhydrous dichloromethane (50 ml) solution of 2,3,4-trimethoxybenzaldehyde (1.96 g, 10 mmol) under argon at room temperature was stirred for 10 min and boron trichloride (10 ml, 10 mmol, 1 eq; 1.0 M solution in dichloromethane) was added. After 2 h, the second equivalent of boron trichloride (10 ml, 10 mmol, 1 eq; 1.0 M solution of dichloromethane) was added. The dark reaction mixture was stirred overnight and then slowly poured into 10% sodium bicarbonate (aq) (4 g/36 ml). The resulting solution was acidified with concentrated hydrochloride acid to pH 1. The dichloromethane layer was separated, and the aqueous layer extracted with ethyl acetate (4×20 ml) and dried. Evaporation of solvent in vacuum gave brown oil, which was further separated by column chromatography (1:1 hexane-ethyl acetate) to afford a yellow solid. Recrystallization from ethyl acetate-hexane gave a pale yellow needle of 48 (1.1 g, 65.5%); Rf0.40 (hexane:ethyl acetate: 1:1).

1. customThe dark reaction mixture
2. customThe dichloromethane layer was separated
3. extractionthe aqueous layer extracted with ethyl acetate (4×20 ml)
4. customdried
5. customEvaporation of solvent in vacuum
6. customgave brown oil, which
7. customwas further separated by column chromatography (1:1 hexane-ethyl acetate)
8. customto afford a yellow solid
9. customRecrystallization from ethyl acetate-hexane

ORDレコード

ord-cca280175d46433885d8985fe95c0af2

出典データセット

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08198302B2