Formaldehyde → Chloromethyl 6-methoxy-6-oxohexanoate

A mixture of 6-methoxy-6-oxohexanoyl chloride (0.040 mole) and paraformaldehyde (0.040 mole) are heated in a sealed vessel at 90 degrees for 3 hours. The reaction is cooled, and the solids are dissolved in dichloromethane. The solution is washed with 5% aqueous sodium bicarbonate, with water, and then with a saturated sodium chloride solution. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo to give crude product, which is purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent. The fractions that contain pure product may be combined and spin evaporated in vacuo to give chloromethyl 6-methoxy-6-oxohexanoate. See Bodor et al., J. Med. Chem., (1980) 23: 469; Ulich et al., J. Am. Chem. Soc., (1921) 43: 660.

1. temperatureare heated in a sealed vessel at 90 degrees for 3 hours
2. temperatureThe reaction is cooled
3. washThe solution is washed with 5% aqueous sodium bicarbonate, with water
4. dry with materialThe organic layer is dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give crude product, which
8. customis purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent
9. customspin evaporated in vacuo

ORD record

ord-5b35738d3a584e1fb8115e5fbc06220b

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763612B2