Furfural → HCID 58860816, compound

Temperature

140 °C

A mixture of 4-bromophenylacetic acid (12.90 g, 60.0 mmol), 2-furancarboxaldehyde (6.0 mL, 72.0 mmol), NEt3 (12.0 mL, 86.4 mmol), and Ac2O (12.0 mL, 127.2 mmol) were heated at 140° C. (bath) with stirring for 1¾ h. The reaction mixture was cooled in an ice bath, before being treated with 2M HCl (30 mL) to adjust the pH to 1. A solid precipitated out of solution. This solid was extracted into Et2O (500 mL). The Et2O layer was washed with H2O (100 mL), before being extracted with 5% w/v aqueous Na2CO3 solution (5×100 mL). The aqueous extracts were washed with Et2O (2×50 mL), before being carefully acidified with AcOH to pH 6. The cream solid generated was collected, washed with H2O, and recrystallised from MeOH—H2O to give the title compound: m/z (ES+)=604.0 [2M+NH4]+.

1. temperatureThe reaction mixture was cooled in an ice bath
2. customA solid precipitated out of solution
3. extractionThis solid was extracted into Et2O (500 mL)
4. washThe Et2O layer was washed with H2O (100 mL)
5. extractionbefore being extracted with 5% w/v aqueous Na2CO3 solution (5×100 mL)
6. washThe aqueous extracts were washed with Et2O (2×50 mL)
7. customThe cream solid generated was collected
8. washwashed with H2O
9. customrecrystallised from MeOH—H2O

ORD record

ord-3bbcd73ddbd948c998975288c58ef0c9

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07214681B2