Hydrochloric Acid → HCID 86093963, compound

Participants

Reaction Conditions

Reaction Steps

390.0 g of isopropanol and 22.4 g (0.59 mol) of sodium borohydride are placed in a one-liter round-bottomed flask with a magnetic stirrer, a thermometer and an addition funnel. 148.4 g (0.59 mol) of 91% methyl 4-formylundecanoate (6) are added dropwise over one hour. The temperature in the bulk rises to 35° C. during the addition. The addition is continued for 29 hours, while allowing the temperature in the bulk to return to room temperature (about 20° C.). After cooling the reaction medium to 5° C., 8.6 g of acetone are added, without exceeding 10° C. in the bulk. The reaction medium is again cooled to 5° C. and 240.0 g of hydrochloric acid are added over one hour, without exceeding 10° C. in the bulk. 250.0 g of water are added to facilitate the separation of the phases. The aqueous phase is extracted twice with 200 ml of toluene. The organic phases are combined and are washed once with 100.0 ml of water and once with 100 ml of brine. The resulting organic phase is dried over magnesium sulfate and filtered. The solvent is evaporated off under reduced pressure (3990 Pa) without exceeding 50° C. in the bulk. 118.0 g (0.42 mol) of 72% 2-heptylpentane-1,5-diol (10) are obtained, and are used directly in the cyclization step.

Provenance & Evidence