Hydrochloric Acid → HCID 57723647, compound

To a solution of 16.9 g (52.2 mmol) of 4,7-dibromo-2,6-dimethyl-1-indanone in 300 ml of THF-methanol (2:1, vol.), 3.80 g (100 mmol) of NaBH4 was added in small portions over 1.5 hours at −5° C. (Caution: temperature must be lower 0° C.). The mixture was stirred overnight at ambient temperature. The resulting mixture was acidified with 10% HCl to pH=4. The organic layer was separated; the aqueous layer was extracted with 3×100 ml of methyl-tert-butyl ether. The combined organic fractions were dried over Na2SO4 and evaporated to dryness. To the residue 500 ml of toluene were added. This toluene solution was treated with pTolSO3H (ca. 5 g) for 2 hours at reflux. Then, one more portion (ca. 5 g) of pTolSO3H was added, and the mixture was refluxed for an additional 2 hours. The resulting mixture was cooled to room temperature and passed through a short Silica Gel 60 column (40-63 μm, d 40 mm, 1 100 mm). This column was additionally eluted with 600 ml of hexanes. The combined extract was evaporated to dryness to give a white solid of the title product. Yield 13.6 g (85%).

1. customThe organic layer was separated
2. extractionthe aqueous layer was extracted with 3×100 ml of methyl-tert-butyl ether
3. dry with materialThe combined organic fractions were dried over Na2SO4
4. customevaporated to dryness
5. additionTo the residue 500 ml of toluene were added
6. additionThis toluene solution was treated with pTolSO3H (ca. 5 g) for 2 hours
7. temperatureat reflux
8. additionThen, one more portion (ca. 5 g) of pTolSO3H was added
9. temperaturethe mixture was refluxed for an additional 2 hours
10. temperatureThe resulting mixture was cooled to room temperature
11. washThis column was additionally eluted with 600 ml of hexanes
12. extractionThe combined extract
13. customwas evaporated to dryness

ORD record

ord-8355abba877c47abb8609293d7cd2b34

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550544B2