Reacción #1617944

Ecuación de reacción

bromoacetic acid

sodium acetate

acetyl chloride

Sodium

triethylene glycol

sodium

→

Isopropyl 11-hydroxy-3,6,9-trioxa-undecanoate

Disolventes

isopropyl alcohol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONAfter 18 hours at 100° C. the excess of diethylene glycol was distilled off at about 4 mm Hg
2. 2
   workup.STIRRINGAfter stirring for 18 hours at 65° C. the mixture
3. 3
   FiltraciónThe mixture was filtered
4. 4
   Otrothe filtrate evaporated nearly to dryness, whereupon it
5. 5
   workup.DISSOLUTIONwas dissolved in water (200 ml)
6. 6
   ExtracciónThe water phase was extracted with 1,1,1-trichloro-ethane (3×50 ml)
7. 7
   LavadoThe pooled organic phases were washed with water (20 ml)
8. 8
   ExtracciónThe product was extracted from the pooled water phases with dichloromethane (50 ml) that
9. 9
   Otroafter evaporation
10. 10
    Otrogave an oil

Procedimiento

Sodium (23 g, 1.0 mole) in form of chips was added in portions to triethylene glycol (700 ml) under nitrogen atmosphere. When the sodium had reacted completely, the mixture was cooled to room temperature and bromoacetic acid was added (76 g, 0.5 mole) under stirring. After 18 hours at 100° C. the excess of diethylene glycol was distilled off at about 4 mm Hg. Thereafter isopropyl alcohol (400 ml) and in portions acetyl chloride (51 g, 0.65 mole) were added. After stirring for 18 hours at 65° C. the mixture was cooled to room temperature and neutralized with sodium acetate (3.5 g, 0.15 mole). The mixture was filtered and the filtrate evaporated nearly to dryness, whereupon it was dissolved in water (200 ml). The water phase was extracted with 1,1,1-trichloro-ethane (3×50 ml). The pooled organic phases were washed with water (20 ml). The product was extracted from the pooled water phases with dichloromethane (50 ml) that after evaporation gave an oil.

Fuente