Synthesis of acetaldehyde 3-bromopropyl ethyl acetal

Preparation of acetaldehyde 3-bromopropyl ethyl acetal

Alternate name: 1-bromo-3-(1-ethoxyethoxy)propane; propane, 1-bromo-3-(1-ethoxyethoxy)-; 3-bromopropyl 1-ethoxyethyl ether

Preparation of acetaldehyde 3-bromopropyl ethyl acetal (1-bromo-3-(1-ethoxyethoxy)propane)

Preparation of acetaldehyde 3-bromopropyl ethyl acetal (1-bromo-3-(1-ethoxyethoxy)propane)

278 g of (pure!) 3-bromopropanol is treated in a 1-liter three-necked flask equipped with a magnetic stirring bar, thermometer, and condenser with drying tube. A 2.75 ml of dichloroacetic acid as a catalyst are added. After the addition, the temperature rises slowly to 50° C over 1 hour period. Additionally 1 ml of dichloroacetic acid is added 1 hour late, and 1 ml again after 4 hours. The obtained solution was left to stir overnight and next day treated with 8 g of powdered sodium carbonate. The mixture was stirred for several hours, filtered, an excess of ethyl vinyl ether removed in vacuo, and obtained residue is purified by fractional distillation in the vacuum with sodium carbonate yielded 379 g (or 92%) of acetaldehyde 3-bromopropyl ethyl acetal as a colorless liquid, bp 49-51° C (1 mm). The acetaldehyde 3-bromopropyl ethyl acetal is sensitive and should be stored at −30° C over powdered sodium carbonate.

J. Org. Chem., 37, 1947, (1972)

IUPAC Name

1-bromo-3-(1-ethoxyethoxy)propane

InChI

InChI=1S/C7H15BrO2/c1-3-9-7(2)10-6-4-5-8/h7H,3-6H2,1-2H3

InChI Key

OGVSYCZHGUMILG-UHFFFAOYSA-N

Canonical SMILES

CCOC(C)OCCCBr

Depositor-Supplied Synonyms

1-Bromo-3-(1-ethoxyethoxy)propane, 34399-67-2, Propane, 1-bromo-3-(1-ethoxyethoxy)-, 3-Bromopropyl 1-ethoxyethyl ether, AC1L3MCZ, AC1Q27X2, SCHEMBL8556930, CTK4H2332, EINECS 251-997-6, AR-1C1957, AKOS024330169, Propane,1-bromo-3-(1-ethoxyethoxy)-, 114596-61-1

Removed Synonyms

CID118164, 35629-13-1

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