Ethyl formate → HCID 13231875, compound

Participants

Reaction Steps

A flask is charged with 75 gr (0.5 mol) 2-chloroindene, 50 ml (0.6 mol) ethyl formate, 400 ml dry ether and 23 gr (0.6 mol) sodium hydride (55-60% dispersion in oil). The mixture is heated to reflux to start the reaction, as indicated by a vigorous hydrogen evolution. The flask is cooled in an ice water bath, until hydrogen evolution subsides, then refluxed again for an additional ten minutes. Excess sodium hydride is carefully decomposed with water, and more water is added to form two layers. The aldehyde dissolves in the aqueous basic solution which is extracted several times with ether. To the aqueous solution are added 19 gr (0.5 mol) sodium borohydride. With vigorous stirring and cooling in an ice water bath, glacial acetic acid is added dropwise at a rate of a drop per second, until the mixture becomes acidic. The alcohol is extracted with ether and the organic solution dried and evaporated. The crude alcohol (75 gr, 83%) is recrystallized from carbon tetrachloride, to give white crystals, m.p. 104°-105° C. Elemental analysis: Calc. for C10H5ClO: C, 66.49%. H, 5.02%. Cl, 19.63% Found: C, 66.20%. H, 5.02%. Cl, 19.90. NMR spectrum (CDCl3, δppm): 2.05 (s, 1H), 3.50 (s, 2H), 4.65 (t, 2H), 7.1-7.6 (m, 4H).

Provenance & Evidence