Compounds from renewable resources

Patent metadata

Field	Value
Publication number	US-10047100-B2
Application number	US-201715474401-A
Country	US
Kind code	B2
Filing date	Mar 30, 2017
Priority date	Apr 8, 2016
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

Compounds of formula III:

and salts thereof are disclosed. Also disclosed are methods for preparing compounds of formula III, intermediates useful for preparing compounds of formula III and methods for preparing compounds and materials from compounds of formula III.

First claim

What is claimed is:

1. A compound of formula III or a salt thereof:

wherein: m is 1 or 2; R is H, (C 1 -C 6 )alkyl, or (C 3 -C 6 )cycloalkyl; and the dashed bond is a single bond or double bond.

2. A compound of formula I or a salt thereof, or a compound of formula II or an enantiomer thereof:

wherein R is R is H, (C 1 -C 6 )alkyl, or (C 3 -C 6 )cycloalkyl and each dashed bond is a single bond or double bond provided no two double bonds of the compound of formula II are cumulated.

3. The compound of claim 2 that is a compound of formula Ia or a salt thereof or an enantiomer thereof or a salt thereof, or a compound of formula II or an enantiomer thereof:

4. The compound of claim 2 that is a compound of formula Ia:

or a salt thereof or an enantiomer or a salt thereof.

5. The compound of claim 2 that is a compound of formula Ic or Id:

or a salt thereof or an enantiomer or a salt thereof.

6. The compound of claim 2 that is a compound of formula Ic or Id:

or an enantiomer thereof.

7. The compound of claim 2 that is a compound of formula II:

or an enantiomer thereof.

8. The compound of claim 2 that is:

or a salt thereof.

9. The compound of claim 2 that is:

or a salt thereof.

10. The compound of claim 2 that is:

or a salt thereof.

11. The compound of claim 2 that is:

or a salt thereof.

12. The compound of claim 2 that is:

or a salt thereof.

13. The compound of claim 2 that is:

14. A composition comprising:

or salts thereof.

15. A method for preparing a compound of claim 2 which is a compound of formula Ic1:

or a salt thereof or an enantiomer or a salt thereof, comprising converting furfuryl alcohol to the compound of formula Ic1 or a salt thereof or an enantiomer or a salt thereof.

16. A method for preparing a compound of claim 2 which is a compound of formula Ic1:

or a salt thereof or an enantiomer or a salt thereof, comprising converting itaconic anhydride to the compound of formula Ic1 or a salt thereof or an enantiomer or a salt thereof.

17. A method for preparing a compound of claim 2 which is a compound of formula IIa:

or enantiomer thereof comprising converting a compound of formula Ic:

or a salt thereof or an enantiomer or a salt thereof to the compound of formula IIa wherein R is H, (C 1 -C 6 )alkyl, or (C 3 -C 6 )cycloalkyl.

18. A method for preparing 2-methylstyrene comprising converting a compound of formula Id:

or a salt thereof or an enantiomer or a salt thereof to 2-methylstyrene, wherein R is H, (C 1 -C 6 )alkyl, or (C 3 -C 6 )cycloalkyl.

19. A method for preparing a compound of claim 2 which is a compound of formula Id:

or a salt thereof or an enantiomer or a salt thereof, comprising converting a compound of formula Ic:

or a salt thereof or an enantiomer or a salt thereof to the compound of formula Id, wherein R is H, (C 1 -C 6 )alkyl, or (C 3 -C 6 )cycloalkyl.

Assignees

• Univ Minnesota

Inventors

• Hoye Thomas R
• Pehere Ashok
• Xu Shu

Classifications

• C08F120/28

  containing no aromatic rings in the alcohol moiety · CPC title

• C08F124/00

  Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F118/00; cyclic anhydrides of unsaturated acids C08F120/00, C08F122/00) · CPC title

• C07D493/04

  Ortho-condensed systems · CPC title

• C07C1/213

  by splitting of esters · CPC title

• C07D493/08

  Bridged systems · CPC title