Hydrochloric Acid → 1-Dodecanol

Participants

Reaction Conditions

Reaction Steps

For purposes of analytical determinations, the process of Example 2 was carried out with sodium boroduteride (NaBD4) To 40 milliliters of absolute ethanol was added about 2.5 grams of NaBD4 (0.05972 mole). The suspension was stirred and about 6.78 grams (0.02986 mole) solid 2-nitro cyclododecan-1-one were added in portions maintaining the temperature at about 15° C. The addition took about 20 minutes and some foaming was evidenced (gas evolution). After the addition was complete, a white, fairly thick precipitate was evident. An additional 10 milliliters of ethanol was added to facilitate stirring. The reaction mass was allowed to warm to room temperature and stirred overnight. The acidification process of the previous examples was followed and the precipitate again disappeared at a pH of 2 after addition of about 100 milliliters of 2% HCl. The solution had a fine white appearance. The ethanol/water was stripped to about 1/2 the starting volume and the water-oil emulsion left was taken up in methylene chloride. After two washings with methylene chloride, the combined organic layers were dried over magnesium sulfate and the solvent stripped off and vacuumed. A yellow oil was recovered which solidified fairly rapidly. The material melts at 40° C. and approximately 6.95 grams of product were recovered. Using the deuterium ions supplied in place of hydride ions from the NaBD4, the nuclear magnetic resonance spectroscopy confirmed the ring opening of the cyclic compound to form a dodecanol having a nitro substituent at the opposite end of the hydroxy function. Furthermore, the analysis confirmed that the carbonyl function had been converted to the hydroxy function.

Provenance & Evidence