Toluene → HCID 66602974, compound

HRID 2097468Notes

Reaction equation

HRID 2097468 reaction equation
C1(C)C=CC=CC=1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][CH2:19]Cl)[CH:10]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH:18]=[CH2:19])[CH:10]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 66602625HCID 66602625, compound

Product 1

HCID 66602974HCID 66602974, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

To 2 L of toluene solution containing 217 g (containing an amount corresponding to 790 mmol) of 4-bromo-2-(2-chloroethoxy)-1-methoxybenzene obtained in Reference example 7-(a) were added 780 ml of 50% aqueous solution of sodium hydroxide and 268 g (789 mmol) of tetrabutylammonium hydrogensulfate under ice-cooling, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into water, the organic layer after separation was washed successively with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained concentrate was applied to distillation under reduced pressure (79 to 83° C./100 Pa) to obtain 122 g of the title compound as a colorless oil. (Yield: 68%)

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe organic layer after separation
  4. washwas washed successively with water
  5. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe obtained concentrate
  8. distillationwas applied to distillation under reduced pressure (79 to 83° C./100 Pa)

Sources & evidence

ORD record
ord-4e8d368ed0d5471286a1c0a0d98a6a63
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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