Ethanol → 7-Ethoxy-3,7-dimethyloctan-1-ol

HRID 2164190

Reaction equation

HRID 2164190 reaction equation
[CH2:1]([OH:3])[CH3:2].C([O:7][CH2:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])(=O)C.[OH-].[K+].[BH4-].[Na+]>O>[CH2:1]([O:3][C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][CH:10]([CH3:17])[CH2:9][CH2:8][OH:7])[CH3:2]

Participants

6

Reactant 4

HCID 702Ethanol3×HCID 9017Citronellyl AcetateHCID 14797Potassium HydroxideHCID 4311764Sodium borohydride

Product 1

HCID 227497647-Ethoxy-3,7-dimethyloctan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

150 Grams of mercuric acetate in 400 ml. of dry ethanol is added to 100 g. of 1-acetoxy-3,7-dimethyloct-6-ene (citronellol acetate) in 200 ml. of dry ethanol cooled in an ice bath. The temperature is allowed to come to room temperature by standing overnight. Then the mixture is cooled to 0°, 100 g. of potassium hydroxide in 1.5 l. of ethanol is added followed by addition of 10 g. of sodium borohydride in small portions. After about 30 minutes at 0°, water (100 ml.) is added and mixture left at room temperature for two hours. The mixture is filtered, filtrate concentrated and extracted with ether. The ethereal extract is washed, dried and evaporated to yield 7-ethoxy-3,7-dimethyloctan-1-ol which is purified by distillation or chromatography.

Workup

  1. customto come to room temperature
  2. temperatureThen the mixture is cooled to 0°
  3. additionfollowed by addition of 10 g
  4. waitAfter about 30 minutes at 0°
  5. waitmixture left at room temperature for two hours
  6. filtrationThe mixture is filtered
  7. concentrationfiltrate concentrated
  8. extractionextracted with ether
  9. extractionThe ethereal extract
  10. washis washed
  11. customdried
  12. customevaporated

Sources & evidence

ORD record
ord-bff02748ab2744c3986ad36e4ce09559
Source dataset
uspto-grants-1979_01
Patent number
US04137273

Linked notes

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