Methanol → HCID 54396535, compound

HRID 1284172Notes

Reaction equation

HRID 1284172 reaction equation
[CH3:1][CH:2]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])[CH2:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:13][O:14][C:8]=2[CH:7]=1.[OH-:21].[K+].[BH4-].[Na+].[CH3:25]O>C([O-])(=O)C.C([O-])(=O)C.[Hg+2]>[CH3:25][O:21][C:18]([CH3:19])([CH3:20])[CH2:17][CH2:16][CH2:15][CH:2]([CH3:1])[CH2:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:13][O:14][C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 887Methanol3×HCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 53792687HCID 53792687, compound

Product 1

HCID 54396535HCID 54396535, compound

Reagents, catalysts & solvents 1

HCID 15337Mercuric acetateCatalyst

Procedure

A solution of 0.862 g (2.93 millimols) of mercury diacetate in 20 cc of absolute methanol is added dropwise, whilst stirring, at 0°-5°C, over the course of 15 minutes, to 0.50 g (1.84 millimols) of 1-(4,8-dimethyl-1,7-nonadienyl)-3,4-methylenedioxybenzene in 10 cc of absolute methanol. The mixture is stirred for a further 30 minutes at 0°-5°C. 0.72 g (12.8 millimols) of potassium hydroxide in 10 cc of methanol, followed by 0.053 g (1.40 millimols) of sodium borohydride, are subsequently added. The mixture is stirred at room temperature over night, the solution is decanted off from the resulting mercury and 50 cc of water are added. The mixture is concentrated by evaporation to 40 cc in a vacuum. The residue is extracted with ether, the extract is washed with water and saturated sodium chloride solution, dried over sodium sulphate and evaporated. After chromatography of the residue on silica gel with hexane/ethyl acetate (98:2), pure 1-(8-methoxy-4,8-dimethyl-1-nonenyl)-3,4-methylenedioxybenzene is obtained as a colourless oil apart from a small amount of starting material. nD20 = 1.5288.

Workup

  1. additionare subsequently added
  2. stirringThe mixture is stirred at room temperature over night
  3. customthe solution is decanted off from the resulting mercury and 50 cc of water
  4. additionare added
  5. concentrationThe mixture is concentrated by evaporation to 40 cc in a vacuum
  6. extractionThe residue is extracted with ether
  7. washthe extract is washed with water and saturated sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-d0e599f1e2094b15b7c6e8372fcf35ef
Source dataset
uspto-grants-1976_08
Patent number
US03978097

Reaction notes

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