Water → HCID 12765967, compound

HRID 2417790Notes

Reaction equation

HRID 2417790 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH3:12][C:13]([CH3:29])([C:26](=[O:28])[CH3:27])[CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O.O>CO>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([CH3:29])([CH3:14])[C:26](=[O:28])[CH3:27])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 10942334Sodium MethoxideHCID 125900172,2-Dimethyl-3-oxobutyl 4-methylbenzene-1-sulfonate

Product 1

HCID 12765967HCID 12765967, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

29.7 g (0.55 mol) of sodium methylate were dissolved in 500 ml of methanol and 70.4 g (0.55 mol) of 4-chlorophenol were added to the solution, whilst stirring. After the mixture had been stirred for 10 minutes, the solvent was distilled off under reduced pressure and the residue was taken up in 100 ml of glycol. This solution was added to a solution of 135 g (0.5 mol) of 2,2-dimethyl-1-tosyloxy-butan-3-one in 200 ml of glycol. The reaction mixture was stirred for 48 hours at 100° to 120° C., and was cooled and stirred into 2,000 ml of water. The mixture was extracted with twice 250 ml of diethyl ether, and the combined organic phases were washed with three times 100 ml of water, once with 100 ml of 10% strength sodium hydroxide solution and again with 100 ml of water, dried over sodium sulphate and distilled. 62.9 g (55.7% of theory) of 1-(4-chlorophenoxy)-2,2-dimethylbutan-3-one of boiling point 135°-140° C./0.4 mm Hg were obtained. ##STR10##

Workup

  1. stirringAfter the mixture had been stirred for 10 minutes
  2. distillationthe solvent was distilled off under reduced pressure
  3. stirringThe reaction mixture was stirred for 48 hours at 100° to 120° C.
  4. temperaturewas cooled
  5. extractionThe mixture was extracted with twice 250 ml of diethyl ether
  6. washthe combined organic phases were washed with three times 100 ml of water, once with 100 ml of 10% strength sodium hydroxide solution and again with 100 ml of water
  7. dry with materialdried over sodium sulphate
  8. distillationdistilled

Sources & evidence

ORD record
ord-c073ec2374664cc5a74c491b50e91581
Source dataset
uspto-grants-1984_09
Patent number
US04470994

Reaction notes

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