3-Methyl-3-buten-1-ol → HCID 20300337, compound

HRID 716495Notes

Reaction equation

HRID 716495 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH:6]([CH3:8])[CH2:5][C:4](=[O:9])[CH2:3]1.[CH3:11][C:12]([CH2:14][CH2:15]O)=[CH2:13]>CC1C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:11][C:12]1[CH2:13][C:4]2([CH2:5][CH:6]([CH3:8])[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3]2)[O:9][CH2:15][CH:14]=1

Participants

5

Reactant 2

HCID 129883-Methyl-3-buten-1-olHCID 133983,3,5-Trimethylcyclohexanone

Product 1

HCID 20300337HCID 20300337, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of p-TSA (20 g, 0.105 mol) and toluene (2 L) was heated to 115° C. To this mixture were added 3,3,5-trimethyl cyclohexanone (1.4 kg, 10 mols) and isoprenol (946 g, 11 mols) and heated further for 3-6 h. Water was removed from the reaction azeotropically. The reaction mixture was then cooled to room temperature. The organic phase was washed with a 5% Na2CO3 solution, washed with water dried and concentrated and distilled further to provide to 4,8,8,10-tetramethyl-1-oxaspiro [5.5] undec-3-ene (1.45 kg) having a purity of 94% (sum of the isomers) for a total yield of 55%.

Workup

  1. temperatureheated further for 3-6 h
  2. customWater was removed from the reaction azeotropically
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. washThe organic phase was washed with a 5% Na2CO3 solution
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. distillationdistilled further

Sources & evidence

ORD record
ord-d8147b7c9ae648678e0de973ad555695
Source dataset
uspto-grants-2015_11
Patent number
US09187709B2

Reaction notes

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