Sodium Chloride → HCID 20484759, compound

Participants

Reaction Steps

Ethyl 2-benzylbenzoate (54.0 g) was dissolved in 100 ml of dichloromethane, and with stirring, 121.3 g of stannic chloride was added while cooling the solution with a mixture of ice and sodium chloride. The mixture was stirred for 1 hour. Subsequently, 86 g of α,α-dichloromethyl methyl ether was added dropwise over 1 hour, and then the mixture was stirred at room temperature for 3 hours. After the reaction, the reaction mixture was poured into 1 liter of ice water, and stirred. The dichloromethane layer was separated, washed with water, a saturated aqueous solution of sodium carbonate and subsequently with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The dichloromethane was distilled off. To the residue was added 250 ml of a saturated aqueous solution of sodium bisulfite, and the mixture was vigorously stirred. The precipitated crystals were collected by filtration, and washed with 100 ml of a saturated aqueous solution of sodium chloride and then with 100 ml of ether. The crystals were then suspended in 500 ml of water, and with stirring, 120 g of sodium carbonate was added little by little over the course of 15 minutes. The mixture was stirred for 2 hours. The separated oily substance was extracted with 300 ml of ether. The ethereal layer was washed with water and dried over anhydrous magnesium sulfate. The ether was distilled off to afford 43.3 g of 4-(2-ethoxycarbonylbenzyl)benzaldehyde as a red oily substance.

Provenance & Evidence