Dichloromethane → HCID 86597500, compound

To a mixture of oxalyl dichloride (18.85 ml) and dichloromethane (60 ml), dimethyl sulfoxide (2.99 ml) was added under a nitrogen atmosphere. The mixture was cooled in an ice-water bath and stirred therein for 15 minutes. 9-Hydroxynonanoic acid methyl ester (2.00 g) was added to the mixture. The mixture was stirred for 1 hour and triethylamine (10.8 ml) was added to the reaction mixture. The reaction mixture was stirred for 1 hour at ambient temperature and poured into a mixture of ethyl acetate (EA) and a saturated aqueous solution of ammonium chloride. The separated organic layer was washed with water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo. The obtained residue was purified by chromatography on silica gel (eluted with 5% EA in n-hexane). The fractions including 8-formylnonanoic acid methyl ester were collected and concentrated in vacuo to give 8-formylnonanoic acid methyl ester (1.69 g) as an oil.

1. additionwas added under a nitrogen atmosphere
2. temperatureThe mixture was cooled in an ice-water bath
3. stirringThe mixture was stirred for 1 hour
4. stirringThe reaction mixture was stirred for 1 hour at ambient temperature
5. washThe separated organic layer was washed with water
6. dry with materialdried over magnesium sulfate
7. filtrationAfter filtration
8. concentrationthe filtrate was concentrated in vacuo
9. customThe obtained residue was purified by chromatography on silica gel (eluted with 5% EA in n-hexane)
10. customwere collected
11. concentrationconcentrated in vacuo

ORD record

ord-53c23a7f19c3409b91d5c63c45261018

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468389B2