Dimethyl Sulfoxide → 2-(3,7-dimethyloctoxy)-5-methoxyterephthalaldehyde

Temperature

-50 °C

A 4 l four-neck flask with condenser, precision glass stirrer, internal thermometer and dropping funnel was initially charged with 176.8 g (1.39 mol) of oxalyl chloride and 450 ml of dichloromethane and cooled to −50° C. To this was added dropwise within 45 min a solution of 253.5 g (3.43 mol) of DMSO in 450 ml of dichloromethane. The mixture was stirred for a further 30 min. A solution of 183.8 g (0.57 mol) of 2,5-bis(hydroxymethyl)-1-(3,7-dimethyloctyl-oxy)-4-methoxybenzene in 500 ml of dichloromethane was then added dropwise over 2.5 h. After addition of 100 ml, a white precipitate formed. After addition of 400 ml of the solution, a further 500 ml of dichloromethane were added. After the addition had been completed, the mixture was stirred for a further 15 min, then 151.8 g (1.5 mol) of triethylamine were added dropwise within 1 h. The mixture was allowed to come to room temperature overnight, then 1500 ml of water were added and the mixture was stirred for 0.5 h. The phases were separated, and the aqueous phase was extracted with 2×300 ml of water. The combined organic phases were washed with 1×500 ml of water and dried over Na2SO4, and the solvent was removed under reduced pressure. 175.6 g (58% of theory) of the product were obtained, which was used for the next stage without further purification and without further characterization.

1. customA 4 l four-neck flask with condenser, precision glass stirrer, internal thermometer and dropping
2. additionAfter addition of 100 ml
3. customa white precipitate formed
4. additionAfter the addition
5. stirringthe mixture was stirred for a further 15 min
6. waitto come to room temperature overnight
7. stirringthe mixture was stirred for 0.5 h
8. customThe phases were separated
9. extractionthe aqueous phase was extracted with 2×300 ml of water
10. washThe combined organic phases were washed with 1×500 ml of water
11. dry with materialdried over Na2SO4
12. customthe solvent was removed under reduced pressure
13. custom175.6 g (58% of theory) of the product were obtained
14. customwhich was used for the next stage without further purification and without further characterization

ORD record

ord-1e35b279395848b1bff1274c6a9b59d1

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884175B2