Triethylamine → HCID 11275184, compound

Temperature

30 °C

1035 g (11 mol) of acetaldehyde dimethyl acetal [purity according to gas chromoaography (GC): 96.5%] and 3.4 g (3 ml, 24 mmol, 0.22 mol%) of boron trifluoride etherate were placed under argon in a 2 l two-necked round flask fitted with a magnetic stirrer, a thermometer and a dropping funnel. 530 g (7.35 mol) of methyl (1-propenyl) ether were added dropwise to the mixture within 2 hours at between 30 and 40° C. with occasional cooling (the reaction was exothermic). After completion of the addition the mixture was stirred for a further 30 minutes at 30° C., then cooled to room temperature. 3 ml of triethylamine were added thereto, the mixture was stirred for 15 minutes and suction filtered. The excess acetaldehyde dimethyl acetal was then distilled off on a Raschig column (50×3 cm) at normal pressure and the residue was fractionated on the same column. This gave at a pressure of 50 mbar a 1st fraction (b.p. 81.5-83.5° C.) consisting of 742 g (60% yield) of 1,1,3-trimethoxy-2-methyl-butane (content according to GC: 96.4%) as a colourless liquid and a 2nd fraction (b.p. 83.5-85° C.) consisting of 87.5 g (6.3% yield) of 1,1,3-trimethoxy-2-butane (content according to GC: 86%), likewise as a colourless liquid, i.e. a total yield of 66.3% of the desired product.

1. customfitted with a magnetic stirrer
2. temperaturewith occasional cooling (the reaction
3. additionAfter completion of the addition the mixture
4. temperaturecooled to room temperature
5. stirringthe mixture was stirred for 15 minutes
6. filtrationsuction filtered
7. distillationThe excess acetaldehyde dimethyl acetal was then distilled off on a Raschig column (50×3 cm) at normal pressure
8. customThis gave at a pressure of 50 mbar a 1st fraction (b.p. 81.5-83.5° C.)

ORD record

ord-33728e98f40f43be8b79f8be528a207f

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05990360