Hydrogen Bromide → 16-Bromohexadecanoic acid

HRID 904238Notes

Reaction equation

HRID 904238 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 30-32% 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 treated with charcoal, 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. additionA methylene chloride solution of the product is treated with charcoal
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customCrystallization of the residue from ether-petroleum ether

Sources & evidence

ORD record
ord-4406194bbd32463bb3498d1321d072a9
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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