Trichloroethanol → 4-Bromobutyric acid, 2,2,2-trichloroethyl ester

HRID 1172271Notes

Reaction equation

HRID 1172271 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[Cl:8][C:9]([Cl:13])([Cl:12])[CH2:10]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:10][C:9]([Cl:13])([Cl:12])[Cl:8])=[O:6]

Participants

5

Reactant 3

HCID 8259TrichloroethanolHCID 758094-Bromobutyric acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 111200754-Bromobutyric acid, 2,2,2-trichloroethyl esterYield 79.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 4-bromobutyric acid (3.34 g, 20.0 mmol) in toluene (50 ml) was added 2,2,2-trichloroethanol (14.94 g, 0.10 mol) and p-toluenesulfonic acid monohydrate (7.60 g, 40.0 mmol) and refluxed with a Dean-Stark trap attached for 6 h. Water was removed continuously. The reaction mixture was cooled to room temperature and concentrated in vacuo. The mixture was added CH2Cl2 (75 ml) and washed with H2O (3×25 ml). The organic layer was dried over Na2SO4, filtered and evaporated in vacuo to leave an oil. The residue was distilled to leave the title compound as a colourless oil (4.77 g, 79.9%) (bp 100° C. at 0.5 mmHg).

Workup

  1. temperaturerefluxed with a Dean-Stark trap
  2. customWater was removed continuously
  3. concentrationconcentrated in vacuo
  4. additionThe mixture was added CH2Cl2 (75 ml)
  5. washwashed with H2O (3×25 ml)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto leave an oil
  10. distillationThe residue was distilled

Sources & evidence

ORD record
ord-56e56c149b744f76a305b57744d4e2b4
Source dataset
uspto-grants-2010_11
Patent number
US07834010B2

Reaction notes

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