Hydrogen Bromide → HCID 20160186, compound

Temperature

5 °C

Adapting a procedure of Büchi and Wüest (J. Org. Chem, 1969, 34, 1122–1123), crotonaldehyde (3 g, 43 mmol) was added dropwise to cone. aq. HBr (5.2 g, 64 mmol) over 5 min at 5° C. under air atmosphere. After 15 min of stirring at 5° C. during which time the mixture changed from colourless to brownish, 1,3-propanediol (8.1 g, 107 mmol) was added and the reaction was stirred at 5° C. for further 0.5 h before allowing it warn to rt, and finally stirring it at rt for 2 h. The crude reaction mixture was then n-heptane extracted (2×200 mL), the combined n-heptane extracts were Na2SO4 dried, evaporated in vacuo and 121JP80 was isolated by Kugelrohr distillation (75° C., 0.18 mmHg) to obtain 124 mg (1.4%) of the title compound as a colourless liquid.

1. additionwas added dropwise to cone
2. stirringthe reaction was stirred at 5° C. for further 0.5 h
3. customwarn to rt
4. stirringfinally stirring it at rt for 2 h
5. customThe crude reaction mixture
6. extractionn-heptane extracted (2×200 mL)
7. customdried
8. customevaporated in vacuo
9. custom121JP80 was isolated by Kugelrohr distillation (75° C., 0.18 mmHg)

ORD record

ord-b2952cce38864106b2d7b07053c495e7

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253186B2