Bromoethene → HCID 20396876, compound

HRID 971967Notes

Reaction equation

HRID 971967 reaction equation
[CH:1](Br)=[CH2:2].[Mg].[CH3:5][C:6]1([CH3:14])[CH2:11][CH:10]([CH3:12])[CH2:9][C:8](=[O:13])[CH2:7]1.[Cl-].[NH4+]>O1CCCC1>[CH:1]([C:8]1([OH:13])[CH2:9][CH:10]([CH3:12])[CH2:11][C:6]([CH3:14])([CH3:5])[CH2:7]1)=[CH2:2]

Participants

6

Reactant 4

HCID 11641BromoetheneHCID 133983,3,5-TrimethylcyclohexanoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 20396876HCID 20396876, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard compound is prepared from 80 g of vinyl bromide and 20 g of magnesium in 1 litre of tetrahydrofuran. To this Grignard compound there are added dropwise at room temperature 100 g of 3,3,5-trimethylcyclohexanone (dihydroisophorone) in 100 ml of tetrahydrofuran. The mixture is held at reflux temperature for 12 hours. The mixture is then cooled, treated with saturated ammonium chloride solution and extracted with ether. The organic phase is washed neutral with saturated sodium chloride solution, dried and evaporated. The crude product is distilled in a high vacuum (55° C./0.1 mm Hg). There are obtained 88.9 g of 1-vinyl-1-hydroxy-3,3,5-trimethyl-cyclohexane.

Workup

  1. temperatureat reflux temperature for 12 hours
  2. temperatureThe mixture is then cooled
  3. extractionextracted with ether
  4. washThe organic phase is washed neutral with saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. distillationThe crude product is distilled in a high vacuum (55° C./0.1 mm Hg)

Sources & evidence

ORD record
ord-77fda890bd6c4ac3b9a164ac9387bc19
Source dataset
uspto-grants-1979_07
Patent number
US04162266

Reaction notes

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