Water → 5-Butoxy-4 methyl-3-decene

HRID 1709145Notes

Reaction equation

HRID 1709145 reaction equation
[CH3:1][C:2]([CH:6]([OH:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:3][CH2:4][CH3:5].[H-].[Na+].[CH2:15](Br)[CH2:16][CH2:17][CH3:18].O>C1(C)C=CC=CC=1>[CH2:15]([O:12][CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:2]([CH3:1])=[CH:3][CH2:4][CH3:5])[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 1633364-Methyl-3-decen-5-ol

Product 1

HCID 541790125-Butoxy-4 methyl-3-deceneYield 77.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
80 °C

Procedure

20 g of 4-methyl-3-decen-5-ol dissolved in 100 ml of toluene are added dropwise at 80° C. over a period of 30 minutes to 6.2 g of a 55-60% sodium hydride dispersion in 100 ml of toluene. The mixture is stirred at 80° C. for 12 hours, then cooled to 50° C. and treated dropwise with a solution of 24.1 g of n-butyl bromide in 50 ml of toluene. The mixture is subsequently held at reflux temperature for 6 hours. For the working-up, the mixture is treated at room temperature with water, the organic layer is separated and washed neutral with water, dried and, after the addition of 0.2 g of potassium carbonate, fractionally distilled There are obtained 20.7 g of 5-butoxy-4 methyl-3-decene of boiling point 60° C./0.03 Torr, nD20 =1.4378. Odour: caramel-like, delicate, fatty-fruity.

Workup

  1. temperaturecooled to 50° C.
  2. temperatureat reflux temperature for 6 hours
  3. customthe organic layer is separated
  4. washwashed neutral with water
  5. customdried
  6. additionafter the addition of 0.2 g of potassium carbonate
  7. distillationfractionally distilled There

Sources & evidence

ORD record
ord-196632fc88b74d888a50641739a08314
Source dataset
uspto-grants-1990_08
Patent number
US04948781

Reaction notes

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