Bromoacetic Acid → Octyl bromoacetate

HRID 326973Notes

Reaction equation

HRID 326973 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=[O:4].[CH2:6](O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]CC>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[Br:1][CH2:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:4]

Participants

5

Reactant 2

HCID 6227Bromoacetic AcidHCID 81741-Decanol

Product 1

HCID 347413Octyl bromoacetateYield 117.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

20 g of bromoacetic acid, 22 g of n-decyl alcohol, and 2.5 g of p-toluenesulfonic acid were added to 150 ml of toluene, and the azeotropic dehydration was carried out for 1.5 hours. After cooling the mixture by allowing it to stand, the toluene was removed under reduced pressure and then vacuum distillation was performed, to obtain 41 g of n-octyl bromoacetate (121° C., 10 mmHg).

Workup

  1. temperatureAfter cooling the mixture
  2. customthe toluene was removed under reduced pressure
  3. distillationvacuum distillation

Sources & evidence

ORD record
ord-2fd91b61bc064e369c0264cdf84b2229
Source dataset
uspto-grants-1993_12
Patent number
US05272050

Reaction notes

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