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All posts Subject: 4-Me 4-hydroxy trans crotonic acid, OTC? Please login to post

yei
(Newbee)
10-11-04 00:16
No 535251
4-Me 4-hydroxy trans crotonic acid, OTC?

4-alkyl 4-hydroxy trans-crotonic acids & their salts are potent GHB receptor ligands. How about an OTC synthesis from levulinic acid?

The problem is slightly tricky, because just heating levulinic acid will produce a lactone with the wrong stereochemistry, even if hydrolyzed.
Molecule: Good, Bad ("CC(O)/C=C/C(=O)O.CC(O)/C=C\C(=O)O")

So here is my idea:

Molecule: ketalize ("CC(=O)CCC(=O)O.C(OCC)(OCC)OCC>>CC(OCC)(OCC)CCC(=O)OCC")
1. convert levulinic acid into its ketal with acid/triethyl or trimethyl orthoformate. Yield 90%

Molecule: pyrolize ("CC(OCC)(OCC)CCC(=O)OCC>>CC(OCC)/C=C/C(=O)OCC.OCC")
2. Pyrolyze the ketal in the presence of acidic catalyst to produce an enol ether, which will isomerize (I think) at the temperature employed (~250 C)to conjugate with the carbonyl group. Yield probably about 90% (so says organicum)

Molecule: hydrolyze ("CC(OCC)/C=C/C(=O)OCC>>CC(O)/C=C/C(=O)O")
3. Hydrolyze the ether and ester under acidic conditions to yield the desired compound. Consume and enjoy. Yield ??

At worst, I suppose this method would produce a racemic mixture, but in actuality, the steric hinderance would probably make the trans-isomer the predominant one. Hopefully.

Ketalization of levulinic acid:
JACS 1955, 4069
Leibig's Annalen 1983, 913
Carbohydrate Research #319,63

I will link the last article shortly.

Would this work?

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	All posts		Subject: 4-Me 4-hydroxy trans crotonic acid, OTC?		Please login to post


		yei (Newbee) 10-11-04 00:16 No 535251				4-Me 4-hydroxy trans crotonic acid, OTC?
						4-alkyl 4-hydroxy trans-crotonic acids & their salts are potent GHB receptor ligands. How about an OTC synthesis from levulinic acid? The problem is slightly tricky, because just heating levulinic acid will produce a lactone with the wrong stereochemistry, even if hydrolyzed. Molecule: Good, Bad ("CC(O)/C=C/C(=O)O.CC(O)/C=C\C(=O)O") So here is my idea: Molecule: ketalize ("CC(=O)CCC(=O)O.C(OCC)(OCC)OCC>>CC(OCC)(OCC)CCC(=O)OCC") 1. convert levulinic acid into its ketal with acid/triethyl or trimethyl orthoformate. Yield 90% Molecule: pyrolize ("CC(OCC)(OCC)CCC(=O)OCC>>CC(OCC)/C=C/C(=O)OCC.OCC") 2. Pyrolyze the ketal in the presence of acidic catalyst to produce an enol ether, which will isomerize (I think) at the temperature employed (~250 C)to conjugate with the carbonyl group. Yield probably about 90% (so says organicum) Molecule: hydrolyze ("CC(OCC)/C=C/C(=O)OCC>>CC(O)/C=C/C(=O)O") 3. Hydrolyze the ether and ester under acidic conditions to yield the desired compound. Consume and enjoy. Yield ?? At worst, I suppose this method would produce a racemic mixture, but in actuality, the steric hinderance would probably make the trans-isomer the predominant one. Hopefully. Ketalization of levulinic acid: JACS 1955, 4069 Leibig's Annalen 1983, 913 Carbohydrate Research #319,63 I will link the last article shortly. Would this work? _{It's good to bee back! Don't trust your computer!!}

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