Water → HCID 23226978, compound

HRID 1956164Notes

Reaction equation

HRID 1956164 reaction equation
[CH3:1][C:2]([CH3:16])([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([CH3:15])[CH:8]=1)[C:3]([OH:5])=O.C(Cl)(=O)C(Cl)=O.O>ClCCCl>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7]([CH2:6][C:2]([CH3:1])([CH3:16])[C:3]2=[O:5])=[CH:8][C:9]=1[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 23227017HCID 23227017, compound

Product 1

HCID 23226978HCID 23226978, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 9.0 g of 2,2-dimethyl-3-(4-methoxy-3-methylphenyl)propanoic acid and 20 mL of oxalyl chloride was prepared and allowed to stir for 2 hours. The volatiles were then removed by evaporation under reduced pressure. The residue was dissolved in 30 mL of carbon disulfide and the solution was added with stirring to a mixture of 7.4 g of aluminum chloride and 30 mL of carbon disulfide. The mixture was allowed to react for 2 hours and was then diluted with 200 mL of 1,2-dichloroethane. Water was added slowly with stirring and, after 2 hours, the mixture was extracted with dichloromethane. The extract was dried over sodium sulfate and concentrated by evaporation under reduced pressure. The residue was distilled to obtain the title compound as a colorless liquid boiling at 90°-95° C. under 1 mm Hg (133 Pascals) pressure.

Workup

  1. customwas prepared
  2. customThe volatiles were then removed by evaporation under reduced pressure
  3. dissolutionThe residue was dissolved in 30 mL of carbon disulfide
  4. additionthe solution was added
  5. stirringwith stirring to a mixture of 7.4 g of aluminum chloride and 30 mL of carbon disulfide
  6. customto react for 2 hours
  7. stirringwith stirring and, after 2 hours
  8. extractionthe mixture was extracted with dichloromethane
  9. dry with materialThe extract was dried over sodium sulfate
  10. concentrationconcentrated by evaporation under reduced pressure
  11. distillationThe residue was distilled

Sources & evidence

ORD record
ord-9992f1fba2d5482d889dbc915c61bed1
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

Loading…