Hydrochloric Acid → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A three neck round bottom flask (250 ml) equipped with a magnetic stirrer was charged with pyridine (37.5 mL), H2O (12.5 ml) and NaOH (0.39 g, 9.8 mmol). 1,1,4,4,6-Pentamethyltetrahydronaphtalene 1 (1.00 g, 4.9 mmol) and KMnO4 (3.12 g, 19.8 mmol) were added successively. The reaction mixture was stirred and heated at 95° C. for 16 h and cooled to 1° C. using an ice-water bath. HCl (6 N, 100 mL) was added to acidify to pH=1 and the product was extracted with EtOAc (5×100 mL), dried over Na2SO4, filtered to give after evaporation 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid 2 (0.65 g, 57% yield) as a white solid.

Provenance & Evidence