Sulfuric Acid → 5-(2-Bromophenyl)-5-oxovaleric acid

HRID 1722334Notes

Reaction equation

HRID 1722334 reaction equation
[OH:1]S(O)(=O)=O.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]#[C:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]>O>[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:1])[CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 147984675-(2-Bromophenyl)-4-pentynoic acid

Product 1

HCID 147984685-(2-Bromophenyl)-5-oxovaleric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Into 20cc of concentrated H2SO4 was dissolved 0.1g (0.4 mmol) of the product of Example 1 to give a brown solution. The solution was allowed to stand at room temperature for 10 minutes. Thereafter, the solution was cooled to 0°C. in an ice bath and ice was then added to it. The solution was then diluted with water and extracted twice with ethyl acetate. The combined extracts were sequentially washed once each with water and brine and then dried (MgSO4). Removal of the solvent under reduced pressure produced a yellow oil which was used without further purification.

Workup

  1. customto give a brown solution
  2. additionice was then added to it
  3. extractionextracted twice with ethyl acetate
  4. washThe combined extracts were sequentially washed once each with water and brine
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent under reduced pressure
  7. customproduced a yellow oil which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-1045f24a4ee14680b71790c76bb6b752
Source dataset
uspto-grants-1989_08
Patent number
US04855324

Reaction notes

Loading…