3-Chloro-2-methyl-1-propene → HCID 23442874, compound

HRID 2119694Notes

Reaction equation

HRID 2119694 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:7][C:6]=1[OH:22])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:25](Cl)[C:26](=[CH2:28])[CH3:27]>CN(C)C=O>[C:1]([C:5]1[CH:10]=[C:9]([O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:7][C:6]=1[O:22][CH2:27][C:26]([CH3:28])=[CH2:25])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 23442865HCID 23442865, compound

Product 1

HCID 23442874HCID 23442874, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen stream, a solution of 0.50 g of 2,5-di-t-butyl-4-trimethylacetoxyphenol in 3 ml of dimethylformamide was added dropwise into a suspension of 0.08 g of oily sodium hydride in 3 ml of dimethylformamide. After stirring for 30 minutes, 0.19 ml of methallyl chloride was added dropwise and the mixture was stirred for 3 hours and allowed to attain room temperature. After the reaction was quenched with a saturated aqueous ammonium chloride solution, the mixture was extracted with water and n-hexane. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate) to give 0.48 g of 2,5-di-t-butyl-4-trimethylacetoxy-1-(2-methyl-2-propenyloxy)benzene as a colorless oil (yield 82%).

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. customto attain room temperature
  3. customAfter the reaction was quenched with a saturated aqueous ammonium chloride solution
  4. extractionthe mixture was extracted with water and n-hexane
  5. washThe organic layers were washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate)

Sources & evidence

ORD record
ord-49329bd29af541e98aca8e55bed21c6a
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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