Preparation of 1-ethoxyisobenzofuran. Mechanistic aspects of the Meerwein ortho-ester reaction

B Mir-Mohamad-Sadeghy…

Index: Mir-Mohamad-Sadeghy, Bagher; Rickborn, Bruce Journal of Organic Chemistry, 1984 , vol. 49, # 9 p. 1477 - 1481

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Citation Number: 10

Abstract

The reaction of 0-ethylphthalidium tetrafluoroborate (1) with excess NaOCH3 in CHBOH gives ortho ester 4 as the major product. The mechanism of formation of this solvent-derived material is explored. A plausible intermediate, 1-ethoxyisobenzofuran (8), has been prepared and isolated in solution; 8 reacts readily with: eg, CH30D to give the mixed ortho ester 5 containing ca. one deuterium/mole. This indicates that 8 reacts by rate-determining ...