3,5-Di-tert-butylsalicylaldehyde synthesis
- Product Name:3,5-Di-tert-butylsalicylaldehyde
- CAS Number:37942-07-7
- Molecular formula:C15H22O2
- Molecular Weight:234.33
Yield:37942-07-7 88%
Reaction Conditions:
Stage #1:2,4-di-tert-Butylphenol with tin(IV) chloride;triethylamine in toluene at 20; for 0.25 h;Inert atmosphere;
Stage #2:formaldehyd in toluene at 80; for 12 h;Inert atmosphere;
Steps:
3,5-di-tert-Butyl-2-hydroxybenzaldehyde (5):
To a solution mixture of 2,4-di-tert-butylphenol (5.00 g, 24.23 mmol) and triethylamine (1.69 mL, 12.12 mmol) in toluene (15 mL) was added SnCl4 (0.28 mL, 2.42 mmol) dropwise under N2. White fumes appeared during the addition and stirring was continued for 15 min at room temperature. Subsequently, paraformaldehyde (1.60 g, 53.31 mmol) was added in a single portion and the mixture was heated at 80 °C for 12 h. After cooling to room temperature, water (50 mL) was added and the residue was extracted with EtOAc (3 × 50 mL). The combined extracts were dried over anhydrous MgSO4, concentrated and chromatographed over SiO2 using CHCl3/ hexane (1:1) as eluent. The first band was collected and the solvent removed under vacuo to give 5 (4.98 g, 88%) as a pale-yellow oil. Spectroscopic data are consistent with previously reported data.2
References:
Werlé, Christophe;Yin, Chih-Juo Madeline;Heinemann, Frank W.;Hauser, Christina;Meyer, Karsten [Tetrahedron Letters,2017,vol. 58,# 28,p. 2715 - 2719] Location in patent:supporting information
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