Réaction #95403

Équation de réaction

hydrochloric acid

3-(9-methoxy-3-hydroxy-5,9-dimethyl-decanoyl)-4-butyrolactone

methanol

methanol

→

aimed compound

Rendement 52.1%

3-[1,9-dimethoxy-5,9-dimethyl-2(E)decenylidene]-4-butyrolactone

Rendement 52.1%

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONThe solvent is distilled off in vacuo
2. 2
   workup.DISSOLUTIONthe residue is dissolved in ether
3. 3
   Lavagethe etheral solution is washed with distilled water
4. 4
   Autredried
5. 5
   workup.DISTILLATIONthe solvent is distilled off
6. 6
   Autrethe residue is purified by column chromatography (adsorbent
7. 7
   workup.ADDITIONKieselgel 60, solvent: a 10:0.1 mixture of benzene and methanol)

Mode opératoire

1 ml of methanol saturated with hydrochloric acid is added to a solution of 1.05 g (0.0033 moles) of 3-(9-methoxy-3-hydroxy-5,9-dimethyl-decanoyl)-4-butyrolactone in 10 ml of dry methanol, and the mixture is allowed to stand at room temperature overnight. The solvent is distilled off in vacuo, the residue is dissolved in ether, the etheral solution is washed with distilled water, dried, the solvent is distilled off, and the residue is purified by column chromatography (adsorbent: Kieselgel 60, solvent: a 10:0.1 mixture of benzene and methanol). 0.54 g (52.1%) of the aimed compound are obtained; Rf =0.8 (developed with a 10:0.2 mixture of benzene and methanol).

Source