PROCESSES AND INTERMEDIATES FOR PREPARING alpha,omega-DICARBOXYLIC ACID-TERMINATED DIALKENE ETHERS

1 - 24 . (canceled)

25 . A process for making a compound of formula (48):

wherein:

R 21 is alkyl;

each R 22 and R 23 is independently alkyl; and

each m is independently 0, 1, 2, 3, or 4;

comprising:

(a) allowing a compound of formula (46):

to react with a Br, Cl, or I source to provide a compound of formula (47):

wherein X 24 is Br, Cl, or I; and

(b) allowing a compound of formula (46) to react with the compound of formula (47) in the presence of base to provide the compound of formula (48).

26 . The process of claim 25 , further comprising allowing a compound of formula (43a):

wherein M is Li or Zn;

to react with an alkyl halide of formula (44):

R 23 —X 23    44

wherein X 23 is Br, Cl, or I;

to provide the compound of formula (45);

and

allowing a compound of formula (45) to react with potassium tert-butoxide to provide a compound of formula (46) wherein R 21 is tert-butyl.

27 . The process of claim 26 , further comprising allowing a compound of formula (41a):

wherein M 22 is Li or Zn;

to react with an alkyl halide of formula (42):

R 22 —X 22    42

wherein X 22 is Br, Cl, or I;

to provide the compound of formula (43);

and

allowing the compound of formula (43) to react with a lithium or zinc deprotonating reagent to provide the compound of formula (43a).

28 . The process of claim 27 , further comprising allowing a compound of formula (41):

to react with a lithium or zinc deprotonating reagent to provide the compound of formula (41a).

29 . A process for making a compound of formula (49)

comprising:

(a) performing the process of claim 25 ;

(b) hydrolyzing the compound of formula (48) in the presence of an alkali metal salt, alkali metal base, alkali metal oxide, alkaline earth metal salt, alkaline earth metal base or alkaline earth metal oxide; and

(c) acidifying the product of step (b) to provide the compound of formula (49).

30 . A process for making a compound of formula (49)

comprising:

(a) performing the process of claim 25 where R 21 is tert-butyl and

(b) allowing the compound of formula (48) to react with trifluoroacetic acid to provide the compound of formula (49).

31 . A process for making a compound of formula (50):

wherein M 1 is Ca 2+ and x is 1;

comprising:

(a) performing the process of claim 29 ; and

(b) allowing the compound of formula (49) to react with CaO or Ca(OH) 2 to provide the compound of formula (50).

32 . A process for making a compound of formula (50):

wherein M 1 is Ca 2+ and x is 1;

comprising:

(a) performing the process of claim 30 ; and

(b) allowing the compound of formula (49) to react with CaO or Ca(OH) 2 to provide the compound of formula (50).

33 . The process of claim 31 , wherein each R 22 is methyl, each R 23 is methyl and each m is 1.

34 . The process of claim 32 , wherein each R 22 is methyl, each R 23 is methyl and each m is 1.

35 . The process of claim 33 , wherein the compound of formula (49) reacts with CaO or Ca(OH) 2 in absolute ethanol at reflux and provides compound (4)

as an ethanolic mixture.

36 . The process of claim 34 , wherein the compound of formula (49) reacts with CaO Ca(OH) 2 in absolute ethanol at reflux and provides compound (4)

as an ethanolic mixture.

37 . The process of claim 35 , further comprising:

allowing the ethanolic mixture to cool to room temperature;

diluting the ethanolic mixture with methyl t-butyl ether;

allowing compound (4) to precipitate from the ethanolic mixture; and

filtering compound (4) from the ethanolic mixture to provide a filtered compound (4).

38 . The process of claim 36 , further comprising:

allowing the ethanolic mixture to cool to room temperature;

diluting the ethanolic mixture with methyl t-butyl ether;

allowing compound (4) to precipitate from the ethanolic mixture; and

filtering compound (4) from the ethanolic mixture to provide a filtered compound (4).

39 . A process for making a hydrate of compound (4), comprising:

performing the process of claim 37 ;

drying the filtered compound (4); and

hydrating the filtered compound (4) to provide the hydrate of compound (4).

40 . A process for making a hydrate of compound (4), comprising:

performing the process of claim 38 ;

drying the filtered compound (4); and

hydrating the filtered compound (4) to provide the hydrate of compound (4).

41 . A process for making a compound of formula (49):

wherein:

each R 22 and R 23 is independently alkyl; and

each m is independently 0, 1, 2, 3, or 4;

comprising:

(a) allowing a compound of formula (41):

to react with a lithium or zinc deprotonating reagent to provide a compound of formula (41a):

wherein M 22 is Li or Zn;

(b) reacting the compound of formula (41a) with an alkyl halide of formula (42):

R 22 —X 22    42

wherein X 22 is Br, Cl, or I;

to provide a compound of formula (43):

(c) allowing the compound of formula (43) to react with a lithium or zinc deprotonating reagent to provide a compound of formula (43a):

wherein M 23 is Li or Zn;

(d) allowing the compound of formula (43a) to react with an alkyl halide of formula (44):

R 23 —X 23    44

wherein X 23 is Br, Cl, or I;

to provide a compound of formula (45):

(e) allowing the compound of formula (45) to react with potassium/c/V-butoxide to provide a compound of formula (46):

where R 21 is tert-butyl;

(f) allowing the compound of formula (46) to react with a Br, Cl, or I source to provide a compound of formula (47):

wherein X 24 is Br, Cl, or I;

(g) allowing the compound of formula (46) to react with the compound of formula (47) in the presence of base to provide a compound of formula (48):

(h) allowing the compound of formula (48) to react with trifluoroacetic acid to provide the compound of formula (49)

42 . A process for making a compound of formula (50):

wherein M 1 is an alkaline earth metal and x is 1 or M 1 is an alkali metal and x is 2;

comprising:

(a) performing the process of claim 29 ;

(b) allowing the compound of formula (49) to react with an aqueous solution of hydroxide or oxide of an alkali metal or earth alkaline metal in water-miscible solvent; and

(c) precipitating the compound of formula (50).

43 . A process for making a compound of formula (50):

wherein M 1 is an alkaline earth metal and x is 1 or M 1 is an alkali metal and x is 2;

comprising:

(a) performing the process of claim 30 ;

(b) allowing the compound of formula (49) to react with an aqueous solution of hydroxide or oxide of an alkali metal or earth alkaline metal in water-miscible solvent; and

(c) precipitating the compound of formula (50).

44 . A process for making a compound of formula (45):

wherein:

R 22 and R 23 are each independently alkyl; and

m is 0, 1, 2, 3, or 4;

comprising:

(a) allowing a compound of formula (41):

to react with a lithium or zinc deprotonating reagent to produce a compound of formula (41a):

wherein M 22 is Li or Zn;

(b) reacting the compound of formula (41a) with an alkyl halide of formula (42):

R 22 —X 22    42

wherein X 22 is Br, Cl, or I;

to provide a compound of formula (43):

(c) allowing the compound of formula (43) to react with a lithium or zinc deprotonating reagent to provide a compound of formula (43a):

wherein M 23 is Li or Zn; and

(d) allowing the compound of formula (43a) with an alkyl halide of formula (44):

R 23 —X 23    44

wherein X 23 is Br, Cl, or I;

to provide the compound of formula (45).