Dimethylformamide → HCID 20396681, compound

The monosodium salt of 5-methylresorcinol prepared in Example 4 and dimethyl formamide (200 ml) were charged under nitrogen gas into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. 1-Chloro-2,2-dimethoxyethane (6.25 grams) was added, and the mixture was heated at 85° to 90° C. and stirred for a period of about 221/2 hours. After this time the reaction mixture was cooled to room temperature and was added to 1200 ml of water. The resulting mixture was carefully neutralized and extracted with chloroform. The organic phase was then separated from the aqueous phase and stripped of solvent, leaving a liquid residue. The residue was distilled under reduced pressure to yield a yellow viscous liquid which solidified upon cooling to -10° C. This product was then recrystallized from a methanol-water mixture, was washed with boiling water and dried to yield the desired product 3-(2,2-dimethoxyethoxy)-5-hydroxytoluene as a white solid melting at 73° to 75° C.

1. customequipped with a mechanical stirrer
2. additionthermometer and addition funnel
3. temperaturethe mixture was heated at 85° to 90° C.
4. extractionextracted with chloroform
5. customThe organic phase was then separated from the aqueous phase
6. customleaving a liquid residue
7. distillationThe residue was distilled under reduced pressure
8. customto yield a yellow viscous liquid which
9. temperatureupon cooling to -10° C
10. customThis product was then recrystallized from a methanol-water mixture
11. washwas washed with boiling water
12. customdried

ORD record

ord-e61ff5139adc425ea1fe5e42b6fe51f5

Source dataset

uspto-grants-1979_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04163112