Dimethyl Sulfate → HCID 12431829, compound

HRID 1362519Notes

Reaction equation

HRID 1362519 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 130420911-(3-Chloro-2-hydroxyphenyl)propan-1-one

Product 1

HCID 12431829HCID 12431829, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3′-Chloro-2′-hydroxypropiophenone (10 g, 54.3 mmol) and potassium carbonate (17.5 g) in 70 ml of acetone are admixed with 7 ml of dimethyl sulphate. The reaction mixture is boiled at reflux for three hours. After it has cooled to room temperature, the batch is subjected to suction filtration through Celite and the filter cake is washed with diethyl ether. After the solvent has been removed on a rotary evaporator, the yellow oil which remains is diluted with 200 ml of diethyl ether and the organic phase is washed with 0.2 M aqueous sodium hydroxide solution (100 ml) and brine (100 ml). The organic phase is dried over sodium sulphate and the solvent is removed on a rotary evaporator. This leaves the desired title compound as a colourless oil (98% yield).

Workup

  1. temperatureat reflux for three hours
  2. filtrationthe batch is subjected to suction filtration through Celite
  3. washthe filter cake is washed with diethyl ether
  4. customAfter the solvent has been removed on a rotary evaporator
  5. additionthe yellow oil which remains is diluted with 200 ml of diethyl ether
  6. washthe organic phase is washed with 0.2 M aqueous sodium hydroxide solution (100 ml) and brine (100 ml)
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-ce78159a31e247a19c2e3ee69eeb30c1
Source dataset
uspto-grants-2011_02
Patent number
US07880042B2

Reaction notes

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