Dimethyl Succinate → 3-Carbomethoxy-4-(3-methoxyphenyl)-3-butenoic acid

Reaction equation

CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O.[C:17]([O:25]C)(=[O:24])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21]>C(O)(C)(C)C>[C:20]([C:19](=[CH:12][C:11]1[CH:14]=[CH:15][CH:16]=[C:9]([O:8][CH3:7])[CH:10]=1)[CH2:18][C:17]([OH:25])=[O:24])([O:22][CH3:23])=[O:21]

Participants

Procedure

To a refluxing suspension of 15.71 g (140 mmol, 1.4 eq) of potassium t-butoxide in 50 ml of t-butylalcohol is dropped in a mixture of 12.17 (100 mmol) of 3-methoxybenzaldehyde and 15.70 ml (120 mmol, 1.2 eq) of dimethyl succinate dissolved in 20 ml of t-butylalcohol. The mixture is refluxed for 3 hours, concentrated in vacuo, acidified to pH ~1 using 1N HCl, and extracted with ethylacetate. The organics are dried (MgSO4) and concentrated in vacuo to give 3-carbomethoxy-4-(3-methoxyphenyl)-3-butenoic acid in the form of a yellow oil which is used directly in the next step.