Short Synthesis of tert-Butyl-Hydroxylated 3,5-Di-tert-butyl-4-hydroxybenzaldehyde:  Synthesis of tert-Butyl-Hydroxylated S-2474

• Published in: Journal of organic chemistry Vol. 68; no. 3; pp. 1128 - 1131
• Main Authors: Inagaki, Masanao, Matsumoto, Saichi, Tsuri, Tatsuo
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.02.2003; Amer Chemical Soc
• Subjects: Antioxidants - chemistry; Antioxidants - metabolism; Antirheumatic Agents - chemical synthesis; Antirheumatic Agents - chemistry; Antirheumatic Agents - pharmacology; Benzaldehydes - chemical synthesis; Benzaldehydes - chemistry; Butylated Hydroxytoluene - chemistry; Butylated Hydroxytoluene - metabolism; Catalysis; Chemistry; Chemistry, Organic; Cyclic S-Oxides - chemical synthesis; Cyclic S-Oxides - chemistry; Cyclic S-Oxides - pharmacology; Exact sciences and technology; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Oxidation-Reduction; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Thiazoles - chemical synthesis; Thiazoles - chemistry; Thiazoles - pharmacology; PULMONARY MICROSOMES; QUINONE METHIDES; REACTIVITY; PNEUMOTOXICITY; EPITHELIAL-CELL LINES; 5-LIPOXYGENASE; INHIBITORS; METABOLITE; MOUSE LUNG; HYDROXYTOLUENE; Phenols; Diol; Aromatic compound; Aldehyde; Chemical synthesis; Benzaldehyde derivatives
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo020587v

We have developed a very short synthesis of tert-butyl-hydroxylated di-tert-butyl-4-hydroxybenzaldehyde in which the HBr-DMSO system is used as an effective oxidant (overall yield of 45% for the entire four-step process from 2-tert-butyl-p-cresol). We also accomplished the synthesis of a major metabolite of the antiarthritic drug candidate S-2474.