Acetic Anhydride → 2-Allylhexanal

Participants

Reaction Conditions

Reaction Steps

1,1-Bis(allyloxy)hexane (118.98 g, 0.60 mol) was dissolved in N,N-dimethylacetamide (320 mL) under a nitrogen atmosphere. To the solution, acetic anhydride (170 mL, 1.80 mol) and maleic acid (3.48 g, 0.03 mol) were added, and the mixture was stirred. The reaction mixture was warmed to 115 to 126° C., stirred at this temperature for 25 hours, and then cooled to 10° C. or lower. To the reaction mixture, toluene (480 mL) and water (720 mL) were added, and a 50% aqueous sodium hydroxide solution (294 mL) was slowly added with stirring to separate an organic layer. The aqueous layer was subjected to extraction with toluene (240 mL), and the extract was combined with the organic layer and then washed with 10% saline (240 mL). The organic layer was dried over sodium sulfate. After filtration, the filtrate was used in the next step without being concentrated or purified.

Provenance & Evidence