3,4-dihydro-2H-pyran-2-carboxylic acid → Oxane-2-carboxylic acid

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Reaction Steps

3,4-Dihydro-2H-pyran-2-carboxylic acid, sodium salt (5.0 g) in water (30 ml) was treated with 10% Palladium on carbon catalyst (0.2 g) and the mixture hydrogenated until there was no further uptake of hydrogen. The mixture was filtered through Kieselguhr, the filtrate passed through a column of `Amberlite IR120(H+), evaporated in vacuo and the residue dissolved in dichloromethane, dried and evaporated to give the title compound as colourless oil. (3.3 g, 76%); (Found: M+, 130.0631. C6H10O3 requires M, 130.0630; νmax (CH2Cl) 3500-2750 (v.br), 1772, 1725 cm-1 ; δH (CDCl3), 1.5-1.7 (4H, m), 1.8-2.1 (2H, m), 3.50-3.59 (1H, m), 3.99-4.14 (2H, m) and 7.28 (1H, br.s).

Provenance & Evidence