Sodium Iodide → p-Nitrobenzyl iodoacetate

Sodium iodide (3.5 g) was slowly added to a stirred solution of 4-nitrobenzyl bromoacetate (5.0 g) in acetone (50 ml) at room temperature over 5 minutes, and the solution was stirred at the same temperature for 2.25 hours. The resultant mixture was evaporated in vacuo, and the residue was dissolved in a mixture of ethyl acetate (40 ml) and water (15 ml). The organic layer was separated, washed with a saturated aqueous solution of sodium chloride and an aqueous solution of sodium thiosulfate in turn, and then dried over anhydrous magnesium sulfate. After the solution was evaporated in vacuo, the residue was allowed to stand in a refrigerator overnight, and triturated with methanol (10 ml) to give crystals (5.25 g) of 4-nitrobenzyl iodoacetate, mp 62.5° to 63.5° C.

1. customThe resultant mixture was evaporated in vacuo
2. dissolutionthe residue was dissolved in a mixture of ethyl acetate (40 ml) and water (15 ml)
3. customThe organic layer was separated
4. washwashed with a saturated aqueous solution of sodium chloride
5. dry with materialan aqueous solution of sodium thiosulfate in turn, and then dried over anhydrous magnesium sulfate
6. customAfter the solution was evaporated in vacuo
7. customto stand in a refrigerator overnight
8. customtriturated with methanol (10 ml)

ORD record

ord-f35c406b8d044bf1b92067081c4e7f47

Source dataset

uspto-grants-1984_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04477447