Water → 2-Butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-

HRID 1759271Notes

Reaction equation

HRID 1759271 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH:8]([OH:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].O>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8](=[O:13])[C:9]([CH3:11])([CH3:12])[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24502Potassium DichromateHCID 127742501-(4-Chlorophenoxy)-3,3-dimethylbutan-2-ol

Product 1

HCID 905182-Butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-Yield 69%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

11.4 g (0.05 mole) of 1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-ol were added to a mixture of 14.7 g (0.05 mole) of potassium dichromate in 12.25 g of sulphuric acid and 73.5 g of water at 30° C., whereupon the temperature rose to about 45° C. The mixture was stirred overnight at room temperature and then extracted three times with ether. The combined organic phases were washed with sodium bicarbonate and water, dried over sodium sulphate and concentrated. 7.8 g (69% of theory) of 1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one of melting point 58° C. were obtained. ##STR25##

Workup

  1. customrose to about 45° C
  2. extractionextracted three times with ether
  3. washThe combined organic phases were washed with sodium bicarbonate and water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bc2e8727d5a94da8b018833d4b25751e
Source dataset
uspto-grants-1982_07
Patent number
US04339612

Reaction notes

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