1-Octanol → Octyl bromoacetate

HRID 258221Notes

Reaction equation

HRID 258221 reaction equation
C1(C)C=CC=CC=1.[Br:8][CH2:9][C:10]([OH:12])=[O:11].[CH2:13](O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:11]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 1140TolueneHCID 6227Bromoacetic Acid

Product 1

HCID 347413Octyl bromoacetateYield 113.4%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

There were added to 150 ml of toluene, 20 g of bromoacetic acid, 20 g of n-octyl alcohol and 2.5 g of p-toluenesulfonic acid, and azeotropical dehydration was carried out for 1.5 hours. After cooling, toluene was distilled off at reduced pressure, and 41 g of n-octyl bromoacetate were obtained by vacuum distillation (110° C., 11 mm Hg).

Workup

  1. temperatureAfter cooling
  2. distillationtoluene was distilled off at reduced pressure

Sources & evidence

ORD record
ord-1dfee39f792048d6a5a26305e468a175
Source dataset
uspto-grants-1993_11
Patent number
US05266453

Reaction notes

Loading…