Process for the Preparation of High Purity Alkyladamanantyl Esters

Patent Process for the Preparation of High Purity Alkyladamanantyl Esters 

Yamamoto etal, US Patent 6,696,595 (February 24, 2004) Assignee Tokuyama Component Utility Semiconductor Component 

Adamantanone (30 g) was dissolved in THE and CH3MgBr (200 ml Imol/liter) added thereto at ambient temperature. After 3 hours pyridine (5 g) and methacrylate acid chloride (26 g) were added and the reaction mixture stirred at 50 °C 3 hours, concentrated, and hexane and 1M NH4OH added to the mixture. The organic phase was separated, washed with 5% NaOH solution, and adjusted to pH 8. The crude product was isolated in 90% by weight. 

The crude sample from Step 1 (100 parts) and 0.05 parts of the decomposition inhibitor, 3-ethyl-3-hydroxymethyloxetane, were distilled at 120 °C at 3 mm Hg through an air cooled condenser containing a 5 cm vigoureux column and the product isolated in 95.3 % yield. 

The decomposition inhibitors are free radical polymerization inhibitors. 

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