6-Aminohexanoic Acid → Methyl 6-aminohexanoate

To a suspension of 6-aminohexanoic acid (10.0 g, 76.2 mmol) in methanol (300 mL), was added 5.51 g of concentrated sulfuric acid. The mixture was heated and reacted for 8 hours, while the water formed along with the progress of esterification distilled off with methanol and 60 mL of methanol was added four times on cue. The reaction mixture was cooled, and the pH of the mixture was adjusted to 6.2 by adding 28% methanol solution of sodium methoxide. The solvent was distilled off, the residue was added to 500 mL of water, and the pH of the mixture was adjusted to 10.3 by adding sodium carbonate. After extraction with 350 mL of dichloromethane for three times, the extract was dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off, thereby to yield methyl 6-aminohexanoate.

1. temperatureThe mixture was heated
2. customformed along with the progress of esterification
3. distillationdistilled off with methanol and 60 mL of methanol
4. additionwas added four times on cue
5. temperatureThe reaction mixture was cooled
6. additionby adding 28% methanol solution of sodium methoxide
7. distillationThe solvent was distilled off
8. additionthe residue was added to 500 mL of water
9. additionby adding sodium carbonate
10. extractionAfter extraction with 350 mL of dichloromethane for three times
11. dry with materialthe extract was dried over anhydrous magnesium sulfate
12. distillationThereafter, the solvent was distilled off

ORD record

ord-875e9a5bee2b4467893503ab28355f04

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07202093B2