ChemicalBook CAS DataBase List Isovaleraldehyde

Isovaleraldehyde synthesis

13synthesis methods

Product Name:Isovaleraldehyde
CAS Number:590-86-3
Molecular formula:C5H10O
Molecular Weight:86.13

By oxidation of isoamyl alcohol.

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Yield:590-86-3 98%

Reaction Conditions:

with chloral hydrate in hexane at 25; for 1.5 h;Inert atmosphere;

Steps:

3

General procedure: A stirred solution of the acetal (2, 3.5 mmol) in dry hexane (5 ml), under dry nitrogen at 25 C, was treated with 1 (1.7 g, 10.6 mmol). The mixture was stirred for 2 h, treated with water, and extracted with dichloromethane (10 ml). The extracts were washed with brine solution, dried (Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography on neutral alumina(50-325 mesh, eluent: 2.5:97.5 ethyl acetate-hexane), to obtain the corresponding carbonyl compound (3). The purity was estimated to be >98% by 1H and 13C NMRspectroscopic analysis. In the case of solid acetals, 0.5 ml of dichloromethane along with hexane was added for added solubility; in the case of thioacetals, 21.2 mmol of 1 was used fo reffective deprotection

References:

Chandrasekhar, Sosale;Shrinidhi, Annadka [Synthetic Communications,2014,vol. 44,# 13,p. 1904 - 1913]