Sodium Carbonate → 3,7-Dimethyl-7-methoxyoctan-2-ol

HRID 1658170Notes

Reaction equation

HRID 1658170 reaction equation
[O:1]1[CH:3]([CH:4]([CH3:13])[CH2:5][CH2:6][CH2:7][C:8]([O:11][CH3:12])([CH3:10])[CH3:9])[CH2:2]1.[C:14](=O)([O-])[O-:15].[Na+].[Na+].[H][H]>[Ni].C(O)(C)C>[CH3:14][O:15][CH2:10]/[C:8](=[CH:7]\[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][OH:1])[CH3:13])/[CH3:9].[CH3:13][CH:4]([CH:3]([OH:1])[CH3:2])[CH2:5][CH2:6][CH2:7][C:8]([O:11][CH3:12])([CH3:9])[CH3:10]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 170303Oxirane, 2-(5-methoxy-1,5-dimethylhexyl)-HCID 178418361HCID 178418361, compound

Product 2

HCID 1620533,7-Dimethyl-7-methoxyoctan-2-olHCID 86733558HCID 86733558, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 186 g, 7, 8-epoxy-2-methoxy-2, 6-dimethyloctane and 5 g sodium carbonate in 100 ccs isopropanol was hydrogenated in the presence of 2 g Raney nickel at 120°C and 150 psi hydrogen pressure over 16 hours. The product was filtered and fractionally distilled to give 75 g methoxy-citronellol and 105 g methoxyelgenol. (R=Methyl). Methoxyelgenol has a marked long lasting sandalwood odour with rose undertones.

Workup

  1. filtrationThe product was filtered
  2. distillationfractionally distilled

Sources & evidence

ORD record
ord-ac2c205664804cdf9a54bab26c31129f
Source dataset
uspto-grants-1976_06
Patent number
US03963648

Reaction notes

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