Synthesis of dibutyl acetal

Preparation of dibutyl acetal (di-n-butyl acetal; 1,1-dibutoxyethane; acetaldehyde, dibutyl acetal; 1,1-di-n-butoxyethane; ethane, 1,1-dibutoxy-)

Preparation of dibutyl acetal (di-n-butyl acetal; 1,1-dibutoxyethane; acetaldehyde, dibutyl acetal; 1,1-di-n-butoxyethane; ethane, 1,1-dibutoxy-)

Preparation of dibutyl acetal (di-n-butyl acetal; 1,1-dibutoxyethane; acetaldehyde, dibutyl acetal; 1,1-di-n-butoxyethane; ethane, 1,1-dibutoxy-)

A mixture of 4.5 ml (44 g) of paraldehyde, 232 ml (187.5 g) of n-butyl alcohol and 5 g of p-toluenesulfonic acid is refluxed for 12 hours. The small amount of aqueous layer (about 1 ml) is removed, and the mixture is washed with a solution of 2.5 g of anhydrous sodium carbonate, then with a mixture of 6% hydrogen peroxide and 10 ml of 10% sodium carbonate solution at 40° C, and finally with water. The mixture is dried over anhydrous potassium carbonate and purified by distillation through an efficient fractionating column (Widmer column, a Hempel column filled with glass or ceramic rings). The fraction (75 g) distilling to 120° C consists largely of n-butyl alcohol, then the temperature rises rapidly to 183° C and the dibutyl acetal is collected at 183-190° C. The yield of dibutyl acetal is 110 g and upon redistillation, the dibutyl acetal boils at 186.5-187.5° C.

A text book of practical organic chemistry, by A. I. Vogel, 327, 1974

IUPAC Name

1-(1-butoxyethoxy)butane

InChI

InChI=1S/C10H22O2/c1-4-6-8-11-10(3)12-9-7-5-2/h10H,4-9H2,1-3H3

InChI Key

SWTCCCJQNPGXLQ-UHFFFAOYSA-N

Canonical SMILES

CCCCOC(C)OCCCC

Depositor-Supplied Synonyms

Dibutyl acetal, Di-n-butyl acetal, 1,1-Dibutoxyethane, Acetaldehyde, dibutyl acetal, 1,1-Di-n-butoxyethane, Ethane, 1,1-dibutoxy-, 6-Methyl-5,7-dioxaundecane, Acetaldehyde dibutyl acetal, 871-22-7, NSC 5314, 1,1′-(Ethylidenebis(oxy))dibutane, EINECS 212-804-0, 1,1′-(Ethylidenebis(oxy))bisbutane, BRN 1698922, Butane, 1,1′-[ethylidenebis(oxy)]bis-, AI3-22404, Butane, 1,1′-(ethylidenebis(oxy))bis-, 1,1′-[ETHYLIDENEBIS(OXY)]DIBUTANE, Ethane,1-dibutoxy-, 1-(1-Butoxyethoxy)butane, AC1L2WP4, AC1Q58TP, WLN: 4OYO4, 1-(1-butoxy-ethoxy)-butane, 1-(1-Butoxyethoxy)butane #, SCHEMBL115527, CTK5F7864, NSC5314, SWTCCCJQNPGXLQ-UHFFFAOYSA-N, NSC-5314, AR-1H2242, Butane,1′-[ethylidenebis(oxy)]bis-, AKOS006274653, LS-7902, Butane,1,1′-[ethylidenebis(oxy)]bis-, Butane, 1,1′-(ethylidenebis(oxy))bis- (9CI)

Removed Synonyms

CID79117, 4-01-00-03105 (Beilstein Handbook Reference), 93363-11-2

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