4-Hydroxybenzaldehyde → Ethyl 2-(4-formylphenoxy)-2-methylpropanoate

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Reaction Steps

4Hydroxybenzaldehyde (24.4 g, Aldrich) was dissolved in absolute ethanol (470 ml) and anhy. K2CO3 (27.6 g) and ethyl 2-bromoisobutyrate (39.0 g, Aldrich) added. The resulting mixture was refluxed overnight, allowed to cool and the solvent removed in vacuo. The residue was suspended in water (300 ml) and extracted with CH2Cl2. The combined organic layers were washed with 1.0N aqu. NaOH and water, then dried over MgSO4. Removal of the solvent in vacuo and vacuum distillation of the residue gave the desired product (18.8 g, bp 110°-118° C./0.1 mm Hg).

Provenance & Evidence