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

ORD record

ord-f4b5f6a4fe134527ba9e89e17fb1866d

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07476682B2