Water → HCID 13736245, compound

Temperature

117.5 °C

(2E)-4-Methylhepta-2,6-dienoic acid (67.74 g) obtained by the method described above was dissolved in N,N-dimethylacetamide (210 mL) under a nitrogen atmosphere. To the solution, acetic anhydride (91 mL, 0.96 mol) and triethylamine (67 mL, 0.48 mol) were added. The reaction mixture was warmed and stirred at 115 to 120° C. for 6 hours. The reaction mixture was cooled to room temperature, and n-hexane (360 mL) and water (540 mL) were added thereto to separate an organic layer. The aqueous layer was subjected to two extractions with hexane (each with 180 mL), and all the organic layers were combined and then washed with a 5% aqueous sodium bicarbonate solution (90 mL) and water (90 mL) in this order. The obtained organic layer was concentrated under reduced pressure, and the residue was distilled (74-76° C., approximately 25 mmHg) to obtain the title compound (39.09 g, colorless oil substance) (overall yield from 1,1-bis(allyloxy)propane: 54%).

1. temperatureThe reaction mixture was warmed
2. temperatureThe reaction mixture was cooled to room temperature
3. customto separate an organic layer
4. extractionThe aqueous layer was subjected to two extractions with hexane (each with 180 mL), and all the organic layers
5. washwashed with a 5% aqueous sodium bicarbonate solution (90 mL) and water (90 mL) in this order
6. concentrationThe obtained organic layer was concentrated under reduced pressure
7. distillationthe residue was distilled (74-76° C., approximately 25 mmHg)

ORD record

ord-698137a18f3149f38efe30336d6fcb6d

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09162971B2