Dimethyl Sulfoxide → HCID 21263620, compound

Temperature

-45 °C

A solution of oxalyl chloride (42 mL) in dry methylene dichloride (750 mL) was cooled under a nitrogen atmosphere to −75° C. Dimethylsulfoxide (72 mL) was added dropwise with stirring, followed after 10 minutes by a solution of 4-(n-heptyloxy)butan-1-ol (75.2 g from below) in methylene dichloride (75 mL). The mixture was stirred and allowed to warm to −45° C., then was again cooled to −75° C. and treated dropwise with triethylamine (292 mL). After the addition was complete, the cooling bath was removed and the mixture was allowed to slowly warm to room temperature and stir one hour. Ice was added, and the product was partitioned between water and methylene dichloride. The solvent was removed with a rotary evaporator, and the residue was dissolved in petroleum ether (500 mL) and the solution was rinsed in water, cold aqueous hydrochloric acid, water, and saturated aqueous sodium bicarbonate. After drying over magnesium sulfate, the solvent was stripped in vacuo, and the residue was distilled to give 57.6 g (77%) of 4-(n-heptyloxy)butanal, b.p. 60° C., 0.26 Torr.

1. stirringThe mixture was stirred
2. temperaturewas again cooled to −75° C.
3. additionAfter the addition
4. customthe cooling bath was removed
5. temperatureto slowly warm to room temperature
6. stirringstir one hour
7. additionIce was added
8. customthe product was partitioned between water and methylene dichloride
9. customThe solvent was removed with a rotary evaporator
10. dissolutionthe residue was dissolved in petroleum ether (500 mL)
11. washthe solution was rinsed in water
12. dry with materialAfter drying over magnesium sulfate
13. distillationthe residue was distilled

ORD record

ord-3776a3bf675c4d388a314fc187c4eb43

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06177073B1