2-Phenylethanol → Ethyl Acetoacetate

Participants

Reaction Steps

In the same manner but replacing 3,4-dimethoxyphenethyl alcohol and aminoacetaldehyde diethyl acetal with equivalent amounts of phenethyl alcohol, Khafagy and Lambooy, cited above, and ethyl acetoacetate, respectively, 1-methyl-1-isochromanacetic acid ethyl ester, νmax CHCI3 1720 cm-1, nmr (CDCI3) δ 1.5, 2.85, is obtained. Likewise, replacement with equivalent amounts of 1-naphthaleneethanol, M. Mousseron and Nguyen-Phuoc-Du. Bull. Soc. Chim. Fr., 91 (1948), and ethyl acetoacetate, gives 1,2-dihydro-4-methyl-4H-naphtho [2,1-c]pyran-4-acetic acid ethyl ester, νmax CHCI3 1720 cm-1, nmr (CDCI3) δ1.5. Hydrogen bromide is a preferred acid catalyst for these latter two preparations.

Provenance & Evidence