Hydrochloric Acid → HCID 68504666, compound

Participants

Reaction Steps

8-(4-tert-Butylphenyl)-6-methyl-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one (30.63 g, 95 mmol) in Et2O (200 ml) was added to a cooled (−40° C.) suspension of LiAlH4 (1.08 g, 28.5 mmol) in Et2O (60 ml). The resulting mixture was allowed to warm to room temperature and stirred for additional 1.5 h. Then 2% HCl (100 ml) was added, the resulting mixture was extracted with CH2Cl2 (4×100 ml). The organic phase was washed with water, dried over MgSO4 and evaporated. The flask was sparged with argon; benzene (300 ml) and p-TSA (0.2 g) were added, and the resulting solution was refluxed with Dean-Stark head (control by TLC, benzene) for 2 h. Then the resulting yellow solution was washed with water, aq. KHCO3, water, dried over MgSO4, passed through silica gel and evaporated. The residue was recrystallized from hexane —Et2O (ca. 10:1) yielding 19.7 g (67.7%) of white crystalline product.

Provenance & Evidence