To a 100 mL, 3-necked, RBF was added the SM ( g, mmol) and DCM (9 mL). The mixture was purged with N2 and cooled to -64 C. Under N2 atmsophere, was added DIBAL-H ( in hexane , mL, mmol). The mixture was stirred at -64 C for 2 h. While maintaining the temp below -65 C, the mixture was quenched with the careful dropwise addition of MeOH ( mL, mmol), followed by sat aq Rochelle salt (5 mL). The mixture was allowed to warm to RT and stir for 30 min. The mixture was diluted with H2O and DCM . The layers were separated and the aq layer was further extracted with DCM . The combined organics were washed with brine, dried ( MgSO4 ), and concentrated to provide the product as a colorless oil. [ g, crude]
Benzoic acid occurs naturally as do its esters in many plant and animal species. Appreciable amounts have been found in most berries (around %). Ripe fruits of several Vaccinium species (., cranberry , V. vitis macrocarpon ; bilberry , V. myrtillus ) contain as much as –% free benzoic acid. Benzoic acid is also formed in apples after infection with the fungus Nectria galligena . Among animals, benzoic acid has been identified primarily in omnivorous or phytophageous species, ., in viscera and muscles of the rock ptarmigan ( Lagopus muta ) as well as in gland secretions of male muskoxen ( Ovibos moschatus ) or Asian bull elephants ( Elephas maximus ).