Hydrochloric Acid → HCID 53966625, compound

Participants

Reaction Conditions

Reaction Steps

20.0 ml (0.185 mol) of 3-methoxyphenol are mixed with 50 ml of toluene. 100 ml (0.200 mol) of a 2 molar LDA solution in cyclohexane/toluene/tetrahydrofuran are added dropwise in the course of 30 minutes, with exclusion of moisture and vigorous stirring. The reaction temperature is increased slowly to 60° C. After 48 hours, this reaction solution is added dropwise to a solution of 21.8 g (0.210 mol) of methyl chloroacetate at room temperature and with exclusion of moisture in the course of 3 hours. The reaction solution is stirred at 60° C. for 1 hour. It is then cooled to -17° C. and a further 100 ml (0.200 mol) of the 2 molar LDA solution in cyclohexane/toluene/tetrahydrofuran are added dropwise in the course of 1 hour. After heating at 60° C. for 24 hours, a further 10.0 ml (0.096 mol) of methyl chloroacetate and 30 ml of the 2 molar LDA solution are added. The pale brown reaction mixture is stirred at 60° C. for 24 hours and then introduced into 300 ml of water. The basic solution is rendered neutral with half-concentrated HCl and is finally extracted by shaking three times with 80 ml of toluene each time. The organic phases are collected and are washed with about 50 ml of water beforehand, before they are dried with MgSO4. After the solvent has been stripped off on a rotary evaporator, a yellow-brown residue is obtained. Working up several times by column chromatography over silica gel using toluene as the mobile phase gives the colorant as a yellow solution of yellow fluorescence in the first runnings and the intermediate methyl (m-methoxyphenoxy)acetate as a yellow solution of blue fluorescence in the main runnings.

Provenance & Evidence