Synthesis of diamyl sulfite

Preparation of diamyl sulfite

Alternative Names: pentyl sulfite; dipentyl sulfite; sulfurous acid, dipentyl ester

Preparation of diamyl sulfite (pentyl sulfite; dipentyl sulfite; sulfurous acid, dipentyl ester)

Preparation of diamyl sulfite (pentyl sulfite; dipentyl sulfite; sulfurous acid, dipentyl ester)

A three-necked flask is fitted with a dropping funnel protected with a calcium chloride tube, a mechanical stirrer, a condenser, which is connected to a trap for absorbing hydrogen chloride. 24.5 ml (40 g) of redistilled (b.p. 78–80° C) thionyl chloride are placed in the flask and 67.5 ml (55 g) of dry n-amyl alcohol in the dropping funnel. The flask is cooled in ice and the diamyl alcohol is added dropwise while stirring over 1 hour. When all n-pentanol has been added the mixture is gently refluxed for 1 hour in order to complete the reaction and remove the residual hydrogen chloride. The crude diamyl sulfite is distilled under normal pressure until the temperature rises to 120° C; then under diminished pressure, collecting the fraction boiling at 111.5° C/5 mm.. The yield of diamyl sulfite is 53 g.

A text book of practical organic chemistry, by A. I. Vogel, 304, 1974

IUPAC Name

dipentyl sulfite

InChI

InChI=1S/C10H22O3S/c1-3-5-7-9-12-14(11)13-10-8-6-4-2/h3-10H2,1-2H3

InChI Key

QHKKGWHSXSIVAJ-UHFFFAOYSA-N

Canonical SMILES

CCCCCOS(=O)OCCCCC

Depositor-Supplied Synonyms

Diamyl Sulfite, Pentyl sulfite, Dipentyl sulfite, 2051-05-0, Sulfurous acid, dipentyl ester, SBB060109, oxypentyl(pentyloxysulfinyl), DIAMYLSULFITE, AC1L3ABX, ACMC-1CD4Q, SCHEMBL776945, MolPort-001-783-764, QHKKGWHSXSIVAJ-UHFFFAOYSA-N, ANW-24116, ZINC05820717, AKOS024390803, TC-112861, D2975, ST51046350, I14-58832, 3B3-078527

Removed Synonyms

CID137299

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