O1CCOCC1.[H][H].CO.[C:11]([C:15]1[CH:20]=[C:19]([CH:21](Cl)[CH3:22])[CH:18]=[C:17]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:16]=1[OH:28])([CH3:14])([CH3:13])[CH3:12]>[Cr]([O-])([O-])=O.[Cu+2].CCCCCC.Cl>[C:11]([C:15]1[CH:20]=[C:19]([CH:21]=[CH2:22])[CH:18]=[C:17]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:16]=1[OH:28])([CH3:14])([CH3:13])[CH3:12]
Eight hundred milliliters of dry CCl4 was cooled to 0° to 5° C. Anhydrous AlCl3, 96.4 grams (0.70 mole) was added followed by the dropwise addition of 50 milliliters (0.70 mole) of acetyl chloride. After the addition of acetyl chloride was completed, 103 grams (0.50 mole) of 2,6-di-t-butylphenol dissolved in 100 milliliters of CCl4 was added over a 1 hour period while maintaining a temperature below 10° C. The mixture was slowly warmed to room temperature and stirred an additional hour. The aluminum chloride/3,5-di-t-butyl-4-hydroxyacetophenone complex was hydrolyzed by pouring the reaction mixture into an excess of cold dilute hydrochloric acid. The lower CCl4 layer was separated, and the solvent was evaporated to obtain 118 grams of 3,5-di-t-butyl-4-hydroxyacetophenone with a 95 percent yield and a melting point of 146 to 148° C. A high pressure autoclave was charged with 100 grams (.403 mole) of 3,5-di-t-butyl-4-hydroxyacetophenone, 500 milliliters of dioxane and 10 grams of copper chromite catalyst. Pressure was raised to 1000 psi, and the mixture was heated to 125° to 135° C. until no more hydrogen was absorbed. The mixture was cooled, the catalyst filtered off and the solvent removed to obtain 96 grams of carbinol with a 95 percent yield and a melting point of 86° to 88° C. The carbinol was quantitatively converted to the 2,6-di-t-butyl-4-(α-chloro)ethylphenol by vigorous stirring of 50 grams (0.20 mole) of the carbinol dissolved in 100 milliliters of hexane with 100 milliliters of concentrated HCl for one hour at room temperature. The hexane layer was separated and the solvent removed. The residue was used in the final step. To the residue of 2,6-di-t-butyl-4-(α-chloro)ethylphenol was added 100 milliliters of pyridine. This solution was refluxed for 30 minutes. The pyridine was then removed by the vacuum distillation. The residue was washed thoroughly with water, then dissolved in a small amount of acetone and recrystallized at -78° C. to obtain 44 grams of 2,6-di-t-butyl-4-vinylphenol with a 95 percent yield of a melting point of 36 to 39° C.
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