Réaction #624780

Équation de réaction

2-Hydroxy-4-methoxybenzaldehyde

1-bromodocosane

potassium carbonate

hydrochloric acid

→

2-docosyloxy-4-methoxybenzyl alcohol

Rendement 64.4%

Solvants

DMF

Chloroform

Conditions de réaction

Traitement

1. 1
   Lavagethe mixture was washed
2. 2
   LavageThe organic layer was washed successively with 1N hydrochloric acid and saturated brine
3. 3
   ConcentrationThe organic layer was concentrated
4. 4
   Lavageslurry-washed with methanol
5. 5
   FiltrationThe precipitate was collected by filtration
6. 6
   Autredried under reduced pressure
7. 7
   AutreThe obtained dried crystals
8. 8
   workup.DISSOLUTIONwere dissolved in THF (150 ml)
9. 9
   workup.ADDITIONsodium borohydride (3.7 g) was added
10. 10
    workup.STIRRINGthe mixture was stirred at 40° C. for 3 hr
11. 11
    workup.ADDITION1N Hydrochloric acid was added to the reaction mixture
12. 12
    Concentrationthe mixture was concentrated
13. 13
    ExtractionThe mixture was extracted with chloroform
14. 14
    Lavagewashed successively with aqueous sodium hydrogen carbonate solution and saturated brine
15. 15
    ConcentrationThe organic layer was concentrated
16. 16
    LavageThe obtained residue was washed with acetonitrile
17. 17
    Filtrationthe precipitate was collected by filtration
18. 18
    Autredried under reduced pressure

Mode opératoire

2-Hydroxy-4-methoxybenzaldehyde (5 g, 32.9 mmol), 1-bromodocosane (16.6 g, 42.7 mmol) and potassium carbonate (14.8 g, 107 mmol) were mixed with DMF (150 ml), and the mixture was stirred at 100° C. for 7 hr. Chloroform (400 ml) and 1N hydrochloric acid (300 ml) were added to the reaction mixture, and the mixture was washed. The organic layer was washed successively with 1N hydrochloric acid and saturated brine. The organic layer was concentrated and slurry-washed with methanol. The precipitate was collected by filtration and dried under reduced pressure. The obtained dried crystals were dissolved in THF (150 ml), sodium borohydride (3.7 g) was added, and the mixture was stirred at 40° C. for 3 hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was concentrated. The mixture was extracted with chloroform, and washed successively with aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was concentrated. The obtained residue was washed with acetonitrile, and the precipitate was collected by filtration and dried under reduced pressure to give 2-docosyloxy-4-methoxybenzyl alcohol (9.8 g).

Source