Hydrogen Bromide → 16-Bromo-1-hexadecanol

HRID 526289Notes

Reaction equation

HRID 526289 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH2:20]>C1CCCCC1>[Br:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:20]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 5211771,16-Dibromohexadecane

Product 1

HCID 275701316-Bromo-1-hexadecanol

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

The diol 14 (1.047 g, 4.05 mmol) was dissolved in cyclohexane (30 mL) and vigorously stirred with 48% HBr (0.5 mL, 4.46 mmol, 1.1 eq.). The mixture was refluxed for 6 h, diluted with water (50 mL) and the phases were separated. The aqueous phase was extracted with a mixture of dichloromethane and methanol (v/v, 4:1 3×20 mL). The combined organic layer was dried over MgSO4. The product was purified by column chromatography with silica gel (6×6 cm, cyclohexane/ethyl acetate, 8:1) and isolated as a white solid. Yield: 4.598 g (96%). Traces of 1,16-dibromohexadecane were also found.

Workup

  1. temperatureThe mixture was refluxed for 6 h
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with a mixture of dichloromethane and methanol (v/v, 4:1 3×20 mL)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. customThe product was purified by column chromatography with silica gel (6×6 cm, cyclohexane/ethyl acetate, 8:1)
  6. customisolated as a white solid

Sources & evidence

ORD record
ord-53d13c8c2ee54d379c2481b21d68c879
Source dataset
uspto-grants-2016_05
Patent number
US09345791B2

Reaction notes

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