Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 14852592, compound

Participants

Reaction Steps

Methyl 5,6-dihydroxyhexanoate (0.32 g, 2.0 mmol),2E,4E -pentadecadienal (0.445 g, 2.0 mmol) and catalytic pyridinium p-toluene sulfonate (PPTS) were refluxed in 10 ml of benzene with a Dean Stark trap for 21 hours. The mixture was cooled, filtered, and concentrated. Flash chromatography with 25:1+20:1 hexane/ethyl acetate provided methyl 2-tetradeca-1E,-3E-dienyl-1, 3-dioxolane-4-butanoate as 21 mg of isomer B as a crystalline solid, 25 mg of isomer A, as a crystalline solid, and 68 mg of a mixture of A and B.

Provenance & Evidence