1,2-Dichloroethane → HCID 23114001, compound

HRID 2376356Notes

Reaction equation

HRID 2376356 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1O.[OH-:11].[Na+].O.[Cl:14][CH2:15][CH2:16]Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[Br:1][CH:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[CH:6][C:7]1([O:11][CH2:16][CH2:15][Cl:14])[CH3:8]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962Water2×HCID 14798Sodium HydroxideHCID 183799822-BroMo-3,5-diMethylphenol

Product 1

HCID 23114001HCID 23114001, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 159952Benzyltributylammonium chlorideCatalyst

Procedure

A mixed solution of 2-bromo-3,5-dimethylphenol obtained in Reference Example 149 (16.3 g, 74.6 mmol) and benzyl-tri-n-butylammonium chloride (23.3 g, 7.46 mmol) in 1,2-dichloroethane (150 mL)-a 8 N aqueous sodium hydroxide solution (26 mL)-water (110 mL), was heated under reflux for 5 hours. Water was added to the reaction solution, which was extracted with ethyl acetate. The combined organic layer was washed with water, a saturated sodium hydrogen carbonate solution, and a saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 16.6 g (yield 90%) of the title compound. Oily matter.

Workup

  1. temperatureunder reflux for 5 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. dry with materiala saturated sodium hydrogen carbonate solution, and a saturated brine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-55dd9842597141fa9ff32c8adee15ec1
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

Loading…