Dimethylformamide → 6-Methoxysalicylaldehyde

The 3-(1-ethoxyethoxy)anisole was dissolved in ether (750 ml) and n-butyllithium (1.6M solution in hexanes; 500 ml) was added dropwise at ambient temperature under nitrogen. The mixture was stirred at ambient temperature for 2 hours, then it was cooled to 10° C. and a solution of dimethylformamide (94 g) in ether (150 ml) was added dropwise. The mixture was stirred at ambient temperature for 2 hours, then poured onto crushed ice. The product was extracted into ether, the combined extracts dried over magnesium sulphate, and the solvents removed in vacuo. The residual oil was dissolved in methanol (500 ml) and the stirred solution was cooled in ice and made strongly acidic by the addition of hydrochloric acid (2M). The resulting solid was collected by filtration, washed with water, dried in vacuo over phosphorus pentoxide and crystallised from petroleum ether (b.p. 60°-80° C.) to give 2-hydroxy-6-methoxybenzaldehyde as pale yellow needles (16 g), m.p. 69°-71° C.

1. temperatureit was cooled to 10° C.
2. stirringThe mixture was stirred at ambient temperature for 2 hours
3. additionpoured
4. customonto crushed ice
5. extractionThe product was extracted into ether
6. dry with materialthe combined extracts dried over magnesium sulphate
7. customthe solvents removed in vacuo
8. dissolutionThe residual oil was dissolved in methanol (500 ml)
9. temperaturethe stirred solution was cooled in ice
10. additionmade strongly acidic by the addition of hydrochloric acid (2M)
11. filtrationThe resulting solid was collected by filtration
12. washwashed with water
13. dry with materialdried in vacuo over phosphorus pentoxide
14. customcrystallised from petroleum ether (b.p. 60°-80° C.)

ORD record

ord-8b4051e1e34148c599f183449d8b1c66

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05767116