Diethyl Ether → HCID 57809449, compound

To a stirred suspension of 3.6 g NaH (90 mmol, 60% in mineral oil) in 200 ml Et2O 16.2 ml (94 mmol) of diethyl 2-methylmalonate was added slowly with cooling. After 2 h stirring at 20 C, solution of 21.2 g (90 mmol) of 2-(bromomethyl)-7-methylnaphthalene (prepared according Gorsane, M.; Martin, R. H.; Bull. Soc. Chim. Belg.; 94; 3; 1985; 205-214.) in 20 ml of THF was added, resulting mixture was stirred overnight and decomposed by addition of saturated NH4Cl solution. Organic phase was separated, aqueous—extracted twice with 100 ml portions of ether. Combined extracts were evaporated, residue was dissolved in 150 ml methanol and solution of KOH (20 g, 360 mmol) was added slowly. Mixture was refluxed for 5 h, then evaporated to dryness and resulting semisolid was dissolved in warm water (300 ml). Solution was extracted three times with 100 ml portions of ether, then acidified carefully by addition of 10% HCl. Precipitate of acid 2 was collected and dried, yielded 18.8 g (76%) of yellowish powder.

1. additionwas added slowly
2. temperaturewith cooling
3. additionwas added
4. customresulting mixture
5. customOrganic phase was separated
6. extractionaqueous—extracted twice with 100 ml portions of ether
7. customCombined extracts were evaporated
8. dissolutionresidue was dissolved in 150 ml methanol
9. temperatureMixture was refluxed for 5 h
10. customevaporated to dryness
11. customresulting semisolid
12. extractionSolution was extracted three times with 100 ml portions of ether
13. additionacidified carefully by addition of 10% HCl
14. customPrecipitate of acid 2 was collected
15. customdried

ORD record

ord-b2486e180efc4611be272d9c247ef624

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07579417B2