Ethanol → HCID 21522957, compound

HRID 918116Notes

Reaction equation

HRID 918116 reaction equation
[Cl:1][C:2]1([Cl:14])[CH:12]2[CH:3]1[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([OH:13])[C:10]=1[CH2:11]2.C(O)C.[H-].[Na+].[H][H].[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25]Br>>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][O:13][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][CH:12]1[C:2]([Cl:14])([Cl:1])[CH:3]1[CH2:4]2

Participants

6

Reactant 5

HCID 702EthanolHCID 178642-BromoethyldimethylamineHCID 24758Sodium hydrideHCID 21522953HCID 21522953, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21522957HCID 21522957, compound

Procedure

To a cooled solution of 2.3g (0.01 mole) of product of Example 2 in 50 ml of anhydrous ethanol 0.48g (0.01 mole) of 50% sodium hydride is added in portions. After the evolution of hydrogen has ceased, 1.5g (0.01 mole) of 2-(dimethylamino) ethyl bromide is added dropwise, and the mixture is refluxed with stirring for 3 hours. The solvent is removed in vacuo, the residue is mixed with 25 ml of water and the mixture extracted with chloroform. The chloroform extract is washed with water, dried (MgSO4), and concd. to give 3-[2-(dimethylamino)ethoxy]-1,1-dichloro-1a, 2,7,7a-tetrahydro[1H]-cyclopropa[b]naphthalene.

Workup

  1. temperaturethe mixture is refluxed
  2. customThe solvent is removed in vacuo
  3. additionthe residue is mixed with 25 ml of water
  4. extractionthe mixture extracted with chloroform
  5. extractionThe chloroform extract
  6. washis washed with water
  7. dry with materialdried (MgSO4), and concd

Sources & evidence

ORD record
ord-fffa347c895e406aa429923173ee3ed7
Source dataset
uspto-grants-1976_07
Patent number
US03969392

Reaction notes

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