Réaction #5718

Équation de réaction

methyl (R)-3-hydroxytetradecanoate

dioxan

sodium hydroxide

→

(R)-3-hydroxytetradecanoic acid

Rendement 98.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGAfter stirring for a further 1.5 hours the resulting suspension
2. 2
   Filtrationwas filtered
3. 3
   Lavagethe filter cake was washed with 1000 ml of dioxan
4. 4
   Filtrationfiltered off
5. 5
   workup.ADDITIONThe filter cake was adjusted to pH 0 by the addition of 650 ml of 1.5N hydrochloric acid
6. 6
   workup.STIRRINGThe suspension was stirred
7. 7
   Filtrationfiltered
8. 8
   Lavagethe filter cake was washed with 3000 ml of water
9. 9
   Autrethe crystals were dried

Mode opératoire

Under nitrogen and while stirring there were added dropwise to a solution of 129.2 g of methyl (R)-3-hydroxytetradecanoate, 1033 ml of dioxan and 122.9 g of 28 percent sodium hydroxide solution. 77.5 ml of methanol were added dropwise to the solution. After stirring for a further 1.5 hours the resulting suspension was filtered and the filter cake was washed with 1000 ml of dioxan and filtered off. The filter cake was adjusted to pH 0 by the addition of 650 ml of 1.5N hydrochloric acid. The suspension was stirred, filtered, the filter cake was washed with 3000 ml of water and the crystals were dried. 119.64 g (98%) of (R)-3-hydroxytetradecanoic acid, m.p. 70.6°-71.4°, were obtained.

Source