Sodium Hydroxide → HCID 76219300, compound

A solution of sodium hydroxide (1.09 g, 27.3 mmol) in water (10 mL) was added to a solution of silver nitrate (2.32 g, 13.65 mmol) in water (15 mL) at ice cold temperature for 15 min. 3-Chloro-4,4-dimethylpent-2-enal (1.0 g, 6.825 mmol) was added dropwise at the same temperature for 15 min. The reaction mixture was allowed to rt and stirred for 1 h. The reaction mixture was poured into ice cooled water and filtered through hyflowgel to remove black particles. The hyflowgel bed was washed with hot water and cooled. The solution was acidified with dil. HCl and the solution was extracted with chloroform (3×100 mL) and the combined organic layer was washed with brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product a white color solid (1.0 g, 91%), mp 146-148° C. 1H NMR (400 MHz, CDCl3): δ 8.02 (1H, br s), 6.11 (1H, s), 1.24 (9H, s); LC-MS (negative ion mode): m/z 161, 163 (M−H)−.