Dimethyl Sulfate → Methyl 2-formylbenzoate

Into a 3-neck 1 liter round bottom flask equipped with a magnetic stirrer, reflux condenser fitted with a drying tube, addition funnel with a septum and a nitrogen inlet, 100 g (0.659 mole) 2-carboxybenzaldehyde, about 140 ml methylene chloride and 162.8 g [122.2 ml (1.291 moles)] dimethylsulfate were placed. The mixture was heated to reflux 135.89 g [187.2 ml (1.343 moles)] triethylamine was added dropwise, maintaining a brisk reflux. After the addition was complete, the resulting gold-colored solution was allowed to cool to room temperature, and then washed with 400 ml water. After the layers were separated, the aqueous phase was extracted with 400 ml methylene chloride. The organic layers were combined and washed with 500 ml of a saturated aqueous sodium bicarbonate solution and with 500 ml water. The organic phase was dried over magnesium sulfate and then concentrated to give 111.5 g of the product as a gold liquid.

1. customInto a 3-neck 1 liter round bottom flask equipped with a magnetic stirrer
2. temperaturereflux condenser
3. temperatureThe mixture was heated
4. additionwas added dropwise
5. temperaturemaintaining a brisk reflux
6. additionAfter the addition
7. washwashed with 400 ml water
8. customAfter the layers were separated
9. extractionthe aqueous phase was extracted with 400 ml methylene chloride
10. washwashed with 500 ml of a saturated aqueous sodium bicarbonate solution and with 500 ml water
11. dry with materialThe organic phase was dried over magnesium sulfate
12. concentrationconcentrated

ORD record

ord-bbf75379a5df42dcaa4e47b2f7db5e4b

Source dataset

uspto-grants-1984_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04479900