Sodium Hydroxide → 3-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid

Participants

Reaction Steps

Add commercially available 5-hydroxymethyl-isophthalic acid diethyl ester (5 g, 19.8 mmol) and NaOH (0.79 g, 19.8 mmol) to ethanol (100 mL). Stir for 4 h at room temperature. Concentrate and pour the residue into water (100 mL) and diethyl ether (100 mL). Separate the aqueous layer and wash it with diethyl ether (40 mL). Acidify the aqueous layer with 5 N HCl to about pH=1. Extract the acidic solution with ethyl acetate (3×40 mL). Wash the combined organic layers with water, saturated aqueous sodium chloride, dry (sodium sulfate) and concentrate to give the title compound as a solid (3.3 g, 74%).

Provenance & Evidence