在强酸催化下醇或烯烃与一氧化碳反应生成多一个碳的羧酸的反应。反应中通常会涉及烷基的重排。由于CO操作比较麻烦,通常将甲酸加入到浓硫酸中代替。
反应中通常涉及烷基迁移,生成热力学更稳定的叔碳正离子,叔碳正离子和CO反应生成酰基正离子,水合生成羧酸。
【Tetrahedron Lett. 1981, 22, 2365】
2,2-Dimethylnonanoic acid (2). To 98% H2SO4 (12 mL) at 5 ℃ was added dropwise 100% formicacid (3.9 mL) over 3 min with stirring. 2-Methyl-2-nonanol 1 (795 mg, 5 mmol) in CCl4 (9 mL) wasadded during 3–5 h with stirring (100 rpm) at 5 ℃. After 5 more min, quenching with 100 g ice andextraction (Et2O) was followed by washing the extracts with 5% Na2CO3. Acidification of the basicsolution, extraction with Et2O and evaporation afforded 935 mg of 2; distillation (Kugelrohr) gave 888 mg of 2 (95%), of 95–100% purity.
【Synth. Commun. 1989, 19, 1945-1954】
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