Pyridine → 3,7,11,15-Tetramethyl-hexadecyl chloroformate

Participants

Reaction Steps

Phytanol (48.8 g, 163.5 mmol), and triphosgene (16.17 g, 54.66 mmol) were dissolve in 300 ml of dichloromethane, stirred and cooled on an ice bath. Anhydrous pyridine (12.93 g, 163.5 mmol) was added dropwise over a period of 1 hour. The reaction mixture was stirred for an additional 1 h at room temperature, and then quickly extracted with extra methylene chloride and ice water. The organic layer was pooled, dried over Na2SO4 and evaporated to dryness to yield 52.22 g (88.7%) of phytanyl chloroformate as yellow liquid. 1H NMR in CDCl3: δ0.83, 0.85, 0.86, 0.88, (4s, each 3H, CH3), 0.91 (d, 3H, J=6.0 Hz, CH3), 0.95-1.40 (m, 20H, CH2), 1.39-1.68 (m, 4H, CH), 1.68-1.88 (m, 1H, OH), 4.27-4.47 (m, 2H, CH2OH).

Provenance & Evidence