Propargyl bromide → 1,2-Dimethoxy-4-[1-(2-propynyloxy)propyl]-benzene

HRID 268049Notes

Reaction equation

HRID 268049 reaction equation
[CH2:1]([CH:3]([OH:14])[C:4]1[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[C:6]([O:7][CH3:8])[CH:5]=1)[CH3:2].[H-].[Na+].[CH2:17](Br)[C:18]#[CH:19]>CN(C)C=O>[CH3:11][O:10][C:9]1[CH:12]=[CH:13][C:4]([CH:3]([O:14][CH2:19][C:18]#[CH:17])[CH2:1][CH3:2])=[CH:5][C:6]=1[O:7][CH3:8]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 28586071-(3,4-Dimethoxyphenyl)propan-1-ol

Product 1

HCID 215531891,2-Dimethoxy-4-[1-(2-propynyloxy)propyl]-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 20.8 g of α-ethylveratryl alcohol in 15 ml of dimethylformamide is added dropwise with stirring to a suspension of 12.5 g of sodium hydride in 75 ml of dimethylformamide. The mixture is stirred for 0.5 hour at room temperature (about 22°C.), and 11.8 g of propargyl bromide are then added dropwise, the temperature not being allowed to exceed 30°C. After stirring for 3 hours at room temperature, the mixture is cooled in a ice-bath to 5°C., decomposed with ice-cold water at a temperature of approximately 15°C. and extracted three times with 150 ml of diethyl ether. The extract is washed neutral with water, dried over sodium sulphate, filtered and the filtrate evaporated to dryness under reduced pressure. The oily residue is chromatographed on silica gel using benzene/ether (9:1 parts by volume) as the elution agent. There is obtained 1,2-dimethoxy-4-[1-(2-propynyloxy)propyl]-benzene; nD24 = 1.5248.

Workup

  1. additionare then added dropwise
  2. customto exceed 30°C
  3. temperaturethe mixture is cooled in a ice-bath to 5°C.
  4. customdecomposed with ice-cold water at a temperature of approximately 15°C.
  5. extractionextracted three times with 150 ml of diethyl ether
  6. washThe extract is washed neutral with water
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customthe filtrate evaporated to dryness under reduced pressure
  10. customThe oily residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-87c7749cb94a4352a91926bb98e4c578
Source dataset
uspto-grants-1976_03
Patent number
US03946040

Reaction notes

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