4-Hydroxybenzaldehyde → Benzaldehyde, 4-(2-hydroxyethoxy)-

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Reaction Steps

2-Bromoethanol (5.8 mL) and potassium carbonate (11.3 g) were successively added to a solution of 4-hydroxybenzaldehyde (5.0 g) in MeCN (100 mL). The resulting mixture was stirred and heated at reflux for 3 days under argon. The reaction mixture was cooled to RT and partitioned between EtOAc (100 mL) and 1M aqueous NaOH solution (100 mL). The organic layer was washed with brine (100 mL). The aqueous layers were combined and extracted with EtOAc (50 mL). The organic layers were combined, dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a yellow oil. Yield 6.4 g.

Provenance & Evidence