Benzene → HCID 70149605, compound

Into a 250 ml round bottom flask fitted with a nitrogen inlet and magnetic stirring bar were placed 32.8 ml of benzene and 2,3-ethylenedioxybenzoic acid (2.96 g, 16.4 mmol). The mixture was stirred into a suspension before adding oxalyl chloride (4.3 ml, 8.88 mmol) via a syringe. The mixture was cooled to 0° and 5 drops of dimethylformamide added. The mixture was allowed to warm to room temperature over 1 hour before concentrating the mixture in vacuo. The residue was taken up in 52.5 ml of anhydrous tetrahydrofuran and cooled to 0° before adding diethylamine (17 ml, 164 mmol) dropwise over 10 minutes. The mixture was then allowed to warm to room temperature and diluted with ethyl acetate. The mixture was washed twice with brine, dried over sodium sulfate, filtered, and concentrated to give 3.71 g of subtitled product (96%) which was used directly in the next step.

1. customInto a 250 ml round bottom flask fitted with a nitrogen inlet and magnetic stirring bar
2. temperatureThe mixture was cooled to 0°
3. concentrationbefore concentrating the mixture in vacuo
4. temperaturecooled to 0°
5. temperatureto warm to room temperature
6. washThe mixture was washed twice with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-f14480480eba4a8e94f42a446ab92795

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376505B1