Ethanol → HCID 66878234, compound

Sodium (1.12 g, 48.6 mmol) was added to ethanol (16 mL). The solution was heated to reflux until all sodium was dissolved. To this solution was added diethyl malonate (3.71 g, 23.19 mmol) in ether (45 mL) and the above 1,2-bis-bromomethyl-4-trifluoromethylbenzene (7.7 g, 23.19 mmol) in ether (45 mL). The mixture was refluxed for 16 hrs and the precipitate was filtered out. The filtrate was evaporated and the residue was treated with water (35 mL) and potassium hydroxide (5.30 g). The mixture was stirred and refluxed for 5 hrs and treated with water (20 mL). The resulting mixture was extracted with ether (50 mL). The aqueous phase was acidified with concentrated hydrochloric acid and cooled in an ice bath. Solids were filtered and washed with water. After air drying, 5-trifluoromethyl-indan-2,2-dicarboxylic acid was obtained (3.08 g). LC-MS showed a single peak, C12H19F3O4 (m/e) calcd 274.0453, obsd 273.0 (M−H).

1. temperatureThe solution was heated
2. dissolutionwas dissolved
3. temperatureThe mixture was refluxed for 16 hrs
4. filtrationthe precipitate was filtered out
5. customThe filtrate was evaporated
6. additionthe residue was treated with water (35 mL) and potassium hydroxide (5.30 g)
7. temperaturerefluxed for 5 hrs
8. additiontreated with water (20 mL)
9. extractionThe resulting mixture was extracted with ether (50 mL)
10. temperaturecooled in an ice bath
11. filtrationSolids were filtered
12. washwashed with water
13. customAfter air drying

ORD record

ord-6a21bbfba77b4aada355fa348c459ffa

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652053B2