2-Chloroisobutyraldehyde
- Molecular FormulaC4H7ClO
- Average mass106.551
Propanal, 2-chloro- 2-methyl-
2-chloro-2-methylpr opionaldehyde
917-93-1
[RN]
PROPANAL,2-CHLORO-2 -METHYL-
Synthesis Reference(s)
Journal of the American Chemical Society, 79, p. 3448, 1957 DOI: 10.1021/ja01570a036
2-Chloro-2-methylpropanal (4).(1)
Isobutyraldehyde
(23.2 g, 0.32 mmol) was added to a two-neck round-bottom flask equipped
with a magnetic stir bar, pressure equalizing funnel and reflux
condenser. Sulfuryl chloride (33.8 g, 0.32 mmol) was then transferred to
the addition funnel and added dropwise at a rate to maintain an
external oil bath temperature below 40 °C. The evolved gases were vented
through a trap containing water (ca. 50 mL). Once the sulfuryl chloride
was added, the reaction was heated to 45 °C with stirring for 1.5 h
then stirred at RT for an additional 2.5 h. The addition funnel and
reflux condenser were replaced with a stopper and a distillation head
fitted with a receiving flask. The crude material was distilled under a
vacuum (95 °C, 115 mmHg). A second distillation was necessary to achieve
the pure material as a colorless liquid (12.48 g, 37%). 1H NMR (CDCl3, 300 MHz) δ = 1.56–1.87 (m, 6 H), 9.42 (s, 1 H) ppm; 13C NMR (CDCl3, 75 MHz) δ = 25.8, 69.3, 194.9 ppm.
REF Stevens, C. L.; Gillis, B. T. J. Am. Chem. Soc. 1957, 79, 3448– 3451, DOI: 10.1021/ja01570a036