Hydrochloric Acid → HCID 12980033, compound

Participants

Reaction Steps

Na (0.35 g, 15 mmol) was added in small pieces under Ar to dry ethanol (7 mL). A solution of 2,4,6-triisopropylthiophenol (3.55 g, 15 mmol) was added to the solution of NaOEt and the resulting mixture stirred for 5 min at RT. Bromoacetaldehyde diethylacetal (2.5 mL, 16.5 mmol, Aldrich) was added dropwise to the solution of Na thiolate and the resulting mixture refluxed for 2 h. After that, it was poured into H2O (100 mL), extracted with CH2Cl2 (3×50 mL), the extracts dried (MgSO4), filtered and evaporated (aspirator). The NMR showed the presence of the product and ca. 15% of bromoacetaldehyde diethylacetal impurity. The crude reaction mixture was refluxed with 2% aq. HCl (20 mL) and acetone (30 mL) for 2 h 10 min. The reaction mixture was extracted with CH2Cl2 (3×50 mL), the extracts were dried (MgSO4), filtered and evaporated. Distillation of the product gave a clear liquid, bp 108–114C/0.5 mm, 3.58 g (85.6%). 1H NMR (CD2Cl2) 9.57 (t, 1H; J=3.4 Hz); 7.00 (s, 2H); 3.86 (septet, 2H; J=7.1 Hz); 3.33 (d, 2H; J=3.4 Hz); 2.87 (septet, 1H; J=7.0 Hz); 1.23 (d, 6H; J=7.0 Hz); 1.22 (d, 12H; J=7.1 Hz).

Provenance & Evidence