Sulfuric Acid → 8-Methoxy-4,8-dimethylnonan-2-ol

HRID 1414821Notes

Reaction equation

HRID 1414821 reaction equation
CO[CH2:3]/[C:4](=[CH:6]\[CH2:7][CH2:8][CH:9]([CH2:11][CH:12]=[O:13])[CH3:10])/[CH3:5].[Mg].[CH3:15]I.S(=O)(=O)(O)O.[CH2:22]([O:24]CC)C>>[CH3:22][O:24][C:4]([CH3:3])([CH3:5])[CH2:6][CH2:7][CH2:8][CH:9]([CH3:10])[CH2:11][CH:12]([OH:13])[CH3:15]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 86734392HCID 86734392, compound

Product 1

HCID 214851258-Methoxy-4,8-dimethylnonan-2-ol

Procedure

A solution of 28 g. of methoxycitronellal in 50 ml. of ether is slowly added dropwise at -20° C. to -10° C. to a Grignard solution prepared from 5.35 g. of magnesium and 28.4 g. of methyl iodide in 100 ml. of diethyl ether. The mixture is then poured onto 100 ml. of ice-water, acidified with dilute aqueous sulfuric acid and extracted twice with diethyl ether. The extracts are washed with semi-saturated and saturated sodium chloride solution, dried over sodium sulfate and evaporated. By distillation in a high vacuum there is obtained pure 8-methoxy-4,8-dimethyl-2-nonanol of boiling point 103° C./0.8 mmHg; nD20 = 1.4451.

Workup

  1. customprepared from 5.35 g
  2. additionThe mixture is then poured onto 100 ml
  3. extractionextracted twice with diethyl ether
  4. washThe extracts are washed with semi-saturated and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. distillationBy distillation in a high vacuum

Sources & evidence

ORD record
ord-7c2509b72b02441d958c6635a3463506
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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