Water → 3,4-Bis(methoxymethoxy)benzaldehyde

Chloromethyl methyl ether (1.2 ml, 15.8 mmol) was added dropwise to a stirred solution containing 3,4-dihydroxybenzaldehyde (1 g, 7.25 mmol) and triethylamine (2 ml) in dimethylformamide (100 ml). After stirring at room temperature for 2 days, water (100 ml) was added to destroy any excess chloromethyl methyl ether. The reaction mixture was extracted with ethyl acetate (2×250 ml). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a brown syrup. The crude mixture was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexanes (1:4) to give first 3,4-bismethoxymethoxybenzaldehyde (0.4 g) as a light yellow syrup, and then the monomethoxymethylated derivatives of 3,4-dihydroxybenzaldehyde.

1. customto destroy any excess chloromethyl methyl ether
2. extractionThe reaction mixture was extracted with ethyl acetate (2×250 ml)
3. washThe combined organic extracts were washed with brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a brown syrup
8. customThe crude mixture was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexanes (1:4)

ORD record

ord-15498dc6aac749799f41f9c64f889f08

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06307070B1