Methyl 2-(2-methylphenyl)acetate → methyl (Z)-3-hydroxy-2-(2-methylphenyl)prop-2-enoate

Participants

Reaction Steps

In a similar to manner to Example 1, methyl (2-methylphenyl)acetate was converted to methyl (E)-3-dimethylamino-2-(2-methylphenyl)prop-2-enoate, bp 125°-7°/0.1 mm, which on cooling gave a crystalline solid, mp 48°-49°. This was then hydrolysed in a similar manner to Example 1, but using Amberlite IR 120 resin instead of Amberlyst 15, to give methyl (Z)-3-hydroxy-2-(2-methylphenyl)prop-2-enoate, obtained as an oil and which had the following nmr spectral data: 2.15(3H,s,Me), 3.67(3H,s,CO2Me), 7.0-7.4(5H,m,ArH and =CH), 11.8(1H,d,OH)

Provenance & Evidence