Lithium Chloride → 2-Chloromethyl-1,1,4,4,6-pentamethyl1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

To a solution of 2-carboxymethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (30 g; 0.115 mol) in benzene (570 g), lead tetraacetate (66 g; 0.149 mol) and anhydrous lithium chloride (11.5 g; 0.271 mol) were added, and the temperature was elevated up to 80° C. After stirring for 6.5 hours, the reaction mixture was washed with water and dilute hydrochloric acid in order. After extraction of the unreacted carboxylic acid with 6% ammonia water, the benzene layer was dried over anhydrous sodium sulfate and concentrated to give 2-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (18.9 g; 0.075 mol). From the ammonia water layer, there was recovered the unreacted carboxylic acid (9.8 g).

Provenance & Evidence