Hydrogen Bromide → Phytanyl Bromide

HRID 2304131Notes

Reaction equation

HRID 2304131 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:3][CH2:4]O.[BrH:22].S(=O)(=O)(O)O>O>[Br:22][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 102459Dihydrophytol

Product 1

HCID 10808570Phytanyl BromideYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 40.0 g (134 mmol) of 3,7,11,15-tetramethyl-1-hexadecanol and 400 mL of 48% hydrobromic acid was slowly added 40 mL of concentrated sulfuric acid. The reaction mixture was heated at 100° C. for 24 h and poured into 1.2 L of water. The mixture was extracted with hexanes, and the combined organic phases were washed with saturated aqueous NaHCO3 and dried over MgSO4. The solution was concentrated to a dark liquid, which was eluted through 3 inches (7.6 cm) of silica with hexanes. Concentration of the eluent yielded a light amber liquid, and bulb-to-bulb distillation gave 40.8 g (84%) of 1-bromo-3,7,11,15-tetramethylhexadecane as a clear, colorless liquid, bp 160-180° C. at 0.06 mm Hg.

Workup

  1. extractionThe mixture was extracted with hexanes
  2. washthe combined organic phases were washed with saturated aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. concentrationThe solution was concentrated to a dark liquid, which
  5. washwas eluted through 3 inches (7.6 cm) of silica with hexanes
  6. customConcentration of the eluent yielded
  7. distillationa light amber liquid, and bulb-to-bulb distillation

Sources & evidence

ORD record
ord-f2b3b1e832d64103b32b6ac9afeb4558
Source dataset
uspto-grants-2002_08
Patent number
US06433359B1

Reaction notes

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