Hydrogen Bromide → 16-Bromohexadecanoic acid

HRID 2058746Notes

Reaction equation

HRID 2058746 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>C(O)(=O)C.C(Cl)Cl>[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

7

Reactant 4

HCID 260Hydrogen BromideHCID 297MethaneHCID 1118Sulfuric AcidHCID 1046616-Hydroxyhexadecanoic acid

Product 1

HCID 62039716-Bromohexadecanoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

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. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customCrystallization of the residue from ether-petroleum ether

Sources & evidence

ORD record
ord-f564179e35ee457286e426fd23cf1135
Source dataset
uspto-grants-1982_03
Patent number
US04318914

Reaction notes

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