1-Butanol → Butyl tribromoacetate

HRID 903985Notes

Reaction equation

HRID 903985 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[Br:6][C:7]([Br:12])([Br:11])[C:8](O)=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:8](=[O:9])[C:7]([Br:12])([Br:11])[Br:6])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 6415Tribromoacetic acid

Product 1

HCID 108860Butyl tribromoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

n-Butanol (7.4 g) and tribromoacetic acid (29.6 g) were dissolved in toluene (100 ml). p-Toluenesulfonic acid (0.7 g) was added, and the solution was heated under reflux in a Dean and Stark apparatus. After 90 minutes water (2 ml) had been collected. The solvent was spun off on a rotary evaporator and the residue was distilled under water pump vacuum, collecting the fraction boiling between 120°-130° C. The fraction was redistilled yielding a colorless oil b.p. 128° C./15-18 mm (31 g).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux in a Dean and Stark apparatus
  3. customAfter 90 minutes water (2 ml) had been collected
  4. customThe solvent was spun off on a rotary evaporator
  5. distillationthe residue was distilled under water pump vacuum
  6. customcollecting the fraction
  7. customboiling between 120°-130° C
  8. distillationThe fraction was redistilled

Sources & evidence

ORD record
ord-d0bb9c4ce7754be2a91e53bf36474671
Source dataset
uspto-grants-1980_10
Patent number
US04229519

Reaction notes

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