Water → HCID 22880248, compound

Participants

Reaction Steps

A mixture of the dioxolanol from Step 3 (46.2 g) in water (50 mL) with p-toluenesulfonic acid mono hydrate (1.3 g) was refluxed for 1 hour. The reaction was allowed to cool to r.t. and extract twice with EtOAc (200+150 mL). To this solution was added t-BuOH (175 mL) and Aliquat® 336. This solution was cooled to 10° C. and then a solution of OXONE® (130 g) in water (800 mL) was added over 30 min. The resulting mixture was stirred at r.t. for 20 h. The reaction mixture was neutralized by carefull and portionwise addition of aqueous saturated NaHCO3 and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give a yellow syrup. 1H NMR(CD3COCD3): δ0.90 (3H, t), 1.49 (3H, s), 1.81 (1 H, m), 1.95 (1H, s, OH), 1.99 (1H, m), 3.17 (3H, s), 8.02 (2H, d), 8.32 (2H, d).

Provenance & Evidence