Acetyl chloride → 4-Carbomethoxy-2-methylbutanoic acid

2-Methylglutaric acid (14.6 g.) and acetyl chloride (26 ml.) are heated in the steam bath for 1 hour. The mixture is concentrated to dryness in vacuo and the residue is evaporated twice from toluene. The residue is dissolved in methanol (4.7 ml.) and heated on the steam bath for 1 hour and concentrated to dryness. The residue is dissolved in a mixture of ether (17 ml.), dicyclohexylamine (16.7 ml.) and hexane (83 ml.). The crystalline salt is filtered off and the filtrate is concentrated to one third volume and chilled. The crystals are filtered and dried to yield 11.3 g. of 4-methoxycarbonyl-2-methyl butanoic acid dicyclohexylamine salt, m.p. 97°-99°. The salt is converted to the free acid by distribution between ethyl acetate and aqueous acid.

1. concentrationThe mixture is concentrated to dryness in vacuo
2. customthe residue is evaporated twice from toluene
3. dissolutionThe residue is dissolved in methanol (4.7 ml.)
4. temperatureheated on the steam bath for 1 hour
5. concentrationconcentrated to dryness
6. dissolutionThe residue is dissolved in a mixture of ether (17 ml.), dicyclohexylamine (16.7 ml.) and hexane (83 ml.)
7. filtrationThe crystalline salt is filtered off
8. concentrationthe filtrate is concentrated to one third volume
9. temperaturechilled
10. filtrationThe crystals are filtered
11. customdried
12. customto yield 11.3 g

ORD record

ord-bf9a3c94245546e7ac6b3b95992830b9

Source dataset

uspto-grants-1978_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04105789