Allyl bromide → HCID 23442858, compound

HRID 2119716Notes

Reaction equation

HRID 2119716 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:18])[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([O:18][CH2:23][CH:22]=[CH2:21])[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 54112049HCID 54112049, compound

Product 1

HCID 23442858HCID 23442858, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen stream, 4.48 g of 3-t-butyl-4-trimethylacetoxyphenol synthesized in Example 15-2) was dissolved in 20 ml of dimethylformamide and a suspension of 0.86 g of oily sodium hydride in 20 ml of dimethylformamide at 0° C. was added dropwise. After stirring for 30 minutes, 1.86 ml of allyl bromide was added dropwise and the solution 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 4.31 g of 3-t-butyl-4-trimethylacetoxy-1-(2-propenyloxy)benzene as a colorless oil (yield 83%).

Workup

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

Sources & evidence

ORD record
ord-17b65d129878479c914807d5ba458d4b
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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