Hydrogen Bromide → 16-Bromohexadecanoic acid

HRID 2057640Notes

Reaction equation

HRID 2057640 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

To a stirred solution of 102 gm. 16-hydroxyhexadecanoic acid in 720 ml. 32% hydrobromic acid in acetic acid is slowly added 180 ml. sulfuric acid. After stirring at room temperature overnight the solution is refluxed for 3 hours. An additional 180 ml. solvent is added and reflux is resumed for an additional 4 hours. The warm solution is slowly poured into 2 l. of stirred ice-water, the precipitate is collected and thoroughly washed with water. Crystallization from acetonitrile yields 16-bromohexadecanoic acid as white crystals.

Workup

  1. temperatureis refluxed for 3 hours
  2. additionsolvent is added
  3. temperaturereflux
  4. waitis resumed for an additional 4 hours
  5. additionThe warm solution is slowly poured into 2 l
  6. customof stirred ice-water, the precipitate is collected
  7. washthoroughly washed with water
  8. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-880352c5f5814eb5aab4c1efde4f5a47
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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