Hydrogen Bromide → 8-Bromooctanoic acid

HRID 1980621Notes

Reaction equation

HRID 1980621 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].[BrH:11]>C1(C)C=CC=CC=1>[Br:11][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 5439777-Octenoic acid2×

Product 1

HCID 5482758-Bromooctanoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 500-ml four-necked flask equipped with hydrogen bromide inlet, thermometer, 7-octenoic acid inlet and oxygen inlet was charged with 10 g of 7-octenoic acid and 50 ml of toluene. After passing air at 20° C. with stirring at a rate of 10 liters per hour for 30 minutes, hydrogen bromide and a solution of 90 g of 7-octenoic acid in 250 ml of toluene were continuously fed with stirring at the rates of 120 ml/hr and 9 l/hr, respectively. After 3 hours of reaction, the reaction mixture was treated in the same manner as described above under (3) (i) to give 139 g (89% yield) of 8-bromocaprylic acid.

Workup

  1. customA 500-ml four-necked flask equipped with hydrogen bromide inlet
  2. customat 20° C.
  3. stirringwith stirring at the rates of 120 ml/hr and 9 l/hr
  4. customAfter 3 hours of reaction
  5. additionthe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-f25f2316a363489690b2f79bbbb39a80
Source dataset
uspto-grants-1985_04
Patent number
US04510331

Reaction notes

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