Diethyl Sulfate → HCID 66921047, compound

HRID 2065866Notes

Reaction equation

HRID 2065866 reaction equation
C(=O)([O-])[O-].[K+].[K+].COC(C)(C)C.S([O:19][CH2:20][CH3:21])(OCC)(=O)=O.[Cl:22][C:23]1[CH:39]=[CH:38][C:26]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:34][C:35](O)=[O:36])=[CH:25][CH:24]=1>O.CN(C)C=O>[Cl:22][C:23]1[CH:39]=[CH:38][C:26]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:34][C:35]([O:19][CH2:20][CH3:21])=[O:36])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 122458712-(2-(4-Chlorophenoxy)phenyl)acetic acid

Product 1

HCID 66921047HCID 66921047, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

After mixing 259.1 g of potassium carbonate (1.88 mol, granular reagent), 985 mL of tert-butyl methyl ether, 493 mL of N,N-dimethylformamide and 202.4 g (1.31 mol) of diethyl sulfate, a mixture of 328.4 g (1.25 mol) of 2-(2-(4-chlorophenoxy)phenyl)acetic acid and 164 mL of N,N-dimethylformamide was added dropwise to the obtained mixture over a period of one hour. The internal temperature of the mixture during the dropwise addition was 25-40° C. Upon completion of the dropwise addition, the obtained mixture was stirred at 25° C. for 12 hours, and completion of the reaction was confirmed by high-performance liquid chromatography. A 1642 mL portion of water was slowly added dropwise to suspend the reaction. The internal temperature of the mixture during the dropwise addition was 25-35° C. The obtained mixture was subjected to liquid separation, and after washing the organic layer with 656 mL of water and 495 mL of brine in that order, the obtained organic layer was subjected to dehydration treatment with anhydrous magnesium sulfate and the treated organic layer was concentrated to obtain 366.4 g of crude ethyl 2-(2-(4-chlorophenoxy)phenyl)acetate as an oil.

Workup

  1. additionwas added dropwise to the obtained mixture over a period of one hour
  2. additionThe internal temperature of the mixture during the dropwise addition
  3. customwas 25-40° C
  4. additionUpon completion of the dropwise addition
  5. customthe reaction
  6. additionThe internal temperature of the mixture during the dropwise addition
  7. customwas 25-35° C
  8. customThe obtained mixture was subjected to liquid separation
  9. washafter washing the organic layer with 656 mL of water and 495 mL of brine in that order
  10. concentrationthe treated organic layer was concentrated

Sources & evidence

ORD record
ord-613dbb7f2ac7468f96d5df995a7553e7
Source dataset
uspto-grants-2012_10
Patent number
US08288564B2

Reaction notes

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