Triethyl Phosphate → Cyclooctanemethanol

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A solution of 8 millimols of cobalt 2-ethylhexoate and 20 millimols of triethylphosphate in 200 ml. of benzene was treated in an autoclave with 1:1 H2 :CO mixture for one hour at 170° C. and 3,700-114 3,750 psig. The autoclave was cooled and vented, and 250 g. of 1,5-cyclooctadiene was added. This mixture was treated with 1:1 H2 :CO at 145°-185° C. and 1,800-3,000 psig. for 3 hours. Distillation of the reactor effluent gave 203 g. of hydroformylation products boiling at 36°-75° C. at 5 mm. Hg pressure and 79 g. of residue. Reduction of a portion of the distilled oxygenated products over a nickel-based catalyst with hydrogen at elevated temperatures and pressures gave a 90% yield of hydroxymethylcyclooctane.

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