Hydrogen Bromide → 16-Bromohexadecanoic acid

HRID 1395705Notes

Reaction equation

HRID 1395705 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].S(=O)(=O)(O)O>C(O)(=O)C>[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 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 1046616-Hydroxyhexadecanoic acid

Product 1

HCID 62039716-Bromohexadecanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 18 g. of 16-hydroxyhexadecanoic acid and 160 g. of 30-34% hydrogen bromide in acetic acid is treated with 32 ml. of concentrated sulfuric acid and stirred at ambient temperature for 18 hours. The solution is stirred under reflux for 7 hours and then poured into 500 ml. of ice-water and filtered. A methylene chloride solution of the product is Darco clarified, dried over magnesium sulfate, and evaporated. Crystallization of the residue from ether-petroleum ether and then acetonitrile affords 16-bromohexadecanoic acid as a white solid.

Workup

  1. additionA mixture of 18 g
  2. temperatureunder reflux for 7 hours
  3. additionpoured into 500 ml
  4. filtrationof ice-water and filtered
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customCrystallization of the residue from ether-petroleum ether

Sources & evidence

ORD record
ord-2bf8d47fa3b749ecb669d7638ae9d68a
Source dataset
uspto-grants-1980_05
Patent number
US04205085

Reaction notes

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