ChemicalBook CAS DataBase List Hexadecane, 1-bromo-3,7,11,15-tetramethyl-

Hexadecane, 1-bromo-3,7,11,15-tetramethyl- synthesis

5synthesis methods

Product Name:Hexadecane, 1-bromo-3,7,11,15-tetramethyl-
CAS Number:2791-57-3
Molecular formula:C20H41Br
Molecular Weight:361.44

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Hexadecane, 1-bromo-3,7,11,15-tetramethyl-

2791-57-3
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Yield:2791-57-3 97%

Reaction Conditions:

with N-Bromosuccinimide;triphenylphosphine in dichloromethane at 0 - 20; for 18 h;Reagent/catalyst;Solvent;Temperature;Time;

Steps:

5 EXAMPLE 5
3,7,11,15-Tetramethylhexadecyl Bromide (Dihydrophytyl Bromide)

EXAMPLE 5
3,7,11,15-Tetramethylhexadecyl Bromide (Dihydrophytyl Bromide)
Method B, with NBS and Triphenyl Phosphine: (0035) A solution of dihydrophytol (Example 4; 42.5 g, 0.143 mol), and triphenyl phosphine (41.14 g, 0.157 mol), in methylene chloride (125 mL) was cooled to 0° C. and N-bromosuccinimide (26.15 g, 0.157 mol) was added in portions keeping the temperature below 10° C. After 18 hours at room temperature, methanol (5 mL) was added and the mixture was allowed to concentrate. The residue was suspended in hexanes and the hexane solution was passed through a column of silica gel and then evaporated to dryness. The product, 49.83 g (97% yield) was obtained as a colorless liquid. Mass spec: m/z 360, 362 (M⁺). Anal. Calcd for C₂₀H₄₁Br: C, 66.46%; H, 11.43%; Br, 22.11%. Found: C, 66.86%; H, 11.28%; Br, 22.21%. ¹H NMR (CDCl₃), δ ppm: 0.85-0.90 (m, 15H), 1.06-1.66 (m, 24H), 3.37-3.47 (m, 2H).

References:

US8471035,2013,B1 Location in patent:Page/Page column 12