Hydrogen Bromide → 16-Bromohexadecanoic acid

HRID 1441146Notes

Reaction equation

HRID 1441146 reaction equation
O[CH2:2][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][C:17]([OH:19])=[O:18].[BrH:20]>C(O)(=O)C.S(=O)(=O)(O)O>[Br:20][CH2:2][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][C:17]([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 1046616-Hydroxyhexadecanoic acid

Product 1

HCID 62039716-Bromohexadecanoic acidYield 92.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A 2 liter three neck round bottom flask, equipped with a mechanical stirrer, reflux condenser and nitrogen inlet, was charged with 177 g (0.63 moles) of 16-hydroxy hexadecanoic acid 1. To this vessel were added 1000 mL (5 moles) of 30% hydrogen bromide in acetic acid and 310 mL of concentrated sulfuric acid. The system was equipped with sequential traps containing a sodium hydroxide pellet trap, a 25% aqueous sodium hydroxide solution trap and a saturated sodium carbonate trap. The reaction stirred overnight at room temperature before it was heated to reflux for six hours. The reaction mixture was cooled, poured over ice water and the precipitated solid was filtered under vacuum. After drying under high vacuum, 196 g of 16-bromohexadecanoic acid was obtained.

Workup

  1. temperaturereflux condenser and nitrogen inlet
  2. customThe system was equipped with sequential traps
  3. additioncontaining a sodium hydroxide pellet trap, a 25% aqueous sodium hydroxide solution trap and a saturated sodium carbonate trap
  4. temperaturewas heated
  5. temperatureto reflux for six hours
  6. temperatureThe reaction mixture was cooled
  7. filtrationthe precipitated solid was filtered under vacuum
  8. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-60f0a8fb33e84a4fbae49f4ad837180f
Source dataset
uspto-grants-1996_03
Patent number
US05502226

Reaction notes

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