Sodium Hydroxide → 4-Hydroxymethyl-1,6-heptadiene

To a stirred solution of 2-allylpent-4-enoic acid ethyl ester (prepared above, 14.5 g, 86.2 mmol) in diethyl ether (125 mL) was added lithium aluminum hydride (3.3 g, 87 mmol) in portions slowly over a 30 minute period to cause vigorous gas evolution. When addition of the lithium aluminum hydride was complete, the reaction mixture was stirred for one more hour a room temperature, then 3.5 mL of water were added very slowly. Then 7 mL of a 10 weight percent solution of sodium hydroxide in water were added, followed by the addition of 10 more mL of water. The precipitated white solid was removed from the colorless solution by filtration. Solvent was removed from the solution at reduced pressure to leave 10.1 g of 2-allylpent-4-en-1-ol as a colorless oil whose structure was confirmed by NMR analyses.

1. customThe precipitated white solid was removed from the colorless solution by filtration
2. customSolvent was removed from the solution at reduced pressure

ORD record

ord-efcdcb0fe50646c8a299ad2c51e7bc84

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08597784B2