Ethanol → HCID 54087525, compound

HRID 2164179Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:5][CH:4]=1)[CH3:2].[OH-].[K+].[BH4-].[Na+].[CH2:24]([OH:26])[CH3:25]>>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH2:15][C:16]([O:26][CH2:24][CH3:25])([CH3:18])[CH3:17])=[CH:5][CH:4]=1)[CH3:2]

Participants

Reactant 4

HCID 702Ethanol3×

HCID 14797Potassium Hydroxide

HCID 4311764Sodium borohydride

HCID 54127646HCID 54127646, compound

Product 1

HCID 54087525HCID 54087525, compound

Procedure

To a solution of 2 g. of 1-(4'-ethylphenyl)thio-3,7-dimethylocta-2,6-diene in 20 ml. of ethanol, cooled to 0°, is added a suspension of 2.3 g. of mercuric acetate in 50 ml. of ethanol over 15 minutes. The reaction mixture is stirred for two hours and then, with cooling, 1.2 g. of potassium hydroxide in 20 ml. of ethanol is added. Then 0.14 g. of sodium borohydride is added in small portions and stirring continued for about 30 minutes. The solution is then decanted, concentrated to half volume, diluted with 100 ml. of water and extracted with ether. The ethereal phase is washed with water, dried over magnesium sulfate and evaporated under reduced pressure to yield 1-(4'-ethylphenyl)thio-7-ethoxy-3,7-dimethyloct-2-ene which is purified by chromatography. ##STR12##

Workup

additionis added
additiona suspension of 2.3 g
temperaturewith cooling
stirringstirring
waitcontinued for about 30 minutes
customThe solution is then decanted
concentrationconcentrated to half volume
additiondiluted with 100 ml
extractionof water and extracted with ether
washThe ethereal phase is washed with water
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-cb49bcd50aaa4a8ebf8a3ddf2de753d8
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04137273

Reaction notes

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