Water → HCID 9815573, compound

A dry THF solution (150 ml) of the crude product, methyl 3-methyl-2-dodecenoate (2′) (E/Z mixture, 98.5 g, 0.435 mol), was added dropwise at room temperature to a stirred suspension of LiAlH4 (16.5 g, 0.435 mol) in dry THF (300 ml). The reaction mixture was heated for 2 hours under reflux. After the mixture was reverted to room temperature, water and 10% sulfuric acid were slowly added in sequence, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then concentrated under vacuum to obtain crude (E)-3-methyl-2-dodecen-1-ol (85.5 g, 99%) as an E/Z mixture. The E/Z ratio of the crude alcohol mixture was found to be 96:4 as a result of 250 MHz 1H-NMR analysis. A portion (50 g) of the residue was subjected to silica gel column chromatography (hexane elution) to obtain 41.3 g (83%) of a pure E isomer (3′).

1. temperatureThe reaction mixture was heated for 2 hours
2. temperatureunder reflux
3. customwas reverted to room temperature
4. extractionthe resulting mixture was extracted with diethyl ether
5. washThe organic layer was washed with water
6. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
7. concentrationconcentrated under vacuum

ORD record

ord-ab3ca52b82744bc6ad2c57be12126d86

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06835846B2