1-Butanol → HCID 54574149, compound

HRID 435563Notes

Reaction equation

HRID 435563 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:17])[CH:6]=[C:7]([CH2:15][CH3:16])[CH:8]([CH3:14])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH3:3].[CH2:18](O)[CH2:19]CC>C(O)(=O)C>[CH2:2]([O:4][C:5](=[O:17])[CH:6]=[C:7]([CH2:15][CH3:16])[CH:8]([CH3:14])[CH2:9][CH:10]=[C:11]([CH3:12])[CH3:13])[CH2:3][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 94099Ethyl 3-ethyl-4,7-dimethyl-2,6-octadienoateHCID 5360545Sodium

Product 1

HCID 54574149HCID 54574149, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
100 °C

Procedure

A solution of 100 mg of sodium in 85 ml of n-butanol is placed in a flask filled with nitrogen and cooled to ca 5° C. At this temperature, 20 g (0.09 mol) of 3-ethyl-4,7-dimethyl-2,6-octadienoic acid ethyl ester are added. The mixture is then warmed to 60° C for 5 hours and to 100° C for 3 hours. For the working-up, the mixture is acidified with a few drops of glacial acetic acid and then the major part of the n-butanol is distilled off on a rotary evaporator. The residue is taken up in n-hexane, washed twice with sodium bicarbonate solution and three times with water, dried over sodium sulphate and evaporated. The crude product (19.3 g) is fractionally distilled. There are obtained 16.4 g (73%) of pure 3-ethyl-4,7-dimethyl-2,6-octadienoic acid n-butyl ester of boiling point 90°-92° C/0.04 mm Hg; nD20 = 1.4677.

Workup

  1. additionfilled with nitrogen
  2. temperaturecooled to ca 5° C
  3. distillationthe major part of the n-butanol is distilled off on a rotary evaporator
  4. washwashed twice with sodium bicarbonate solution and three times with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. distillationThe crude product (19.3 g) is fractionally distilled

Sources & evidence

ORD record
ord-fee5b30617da41a797df337a1bcbbd48
Source dataset
uspto-grants-1977_02
Patent number
US04006108

Reaction notes

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