Diisopropyl Ether → HCID 20449319, compound

HRID 1156494Notes

Reaction equation

HRID 1156494 reaction equation
[OH-].[K+].C(OC(C)C)(C)C.[CH:10]#[C:11][CH:12]([OH:14])[CH3:13].[CH2:15]([CH:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]1=[O:25])[CH3:16]>O>[CH2:15]([CH:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]1=[O:25])[CH3:16].[CH2:15]([CH:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]1([OH:25])[C:10]#[C:11][CH:12]([OH:14])[CH3:13])[CH3:16]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 14797Potassium HydroxideHCID 162393-Butyn-2-olHCID 13887928HCID 13887928, compound

Product 2

HCID 13887928HCID 13887928, compoundHCID 20449319HCID 20449319, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

448 g (8 mole) of KOH and 1100 ml of di-isopropyl-ether were first introduced into a reaction vessel fitted with cooling and stirring devices. 154 g (2.2 mole) of but-1-yn-3-ol were then added to the above mixture (temperature 25°-30°; addition period:30 min), followed by 308 g (2.0 mole) of 2-ethyl-6,6-dimethyl-cyclohexanone (addition period:30 min; dropwise). The reaction mixture was then stirred at 35° for 17 hours and, after cooling, 500 ml of water were progressively added thereto. After separation of the organic phase, washing with 5% aqueous H2SO4 (200 ml), drying over Na2SO4, concentration and final distillation, there were isolated a first portion of unreacted 2-ethyl-6,6-dimethyl-cyclohexanone (46 g) and 313 g (78% yield) of 2-ethyl-6,6-dimethyl-1-hydroxyl-1-(3-hydroxy-but-1-yn-1-yl)-cyclohexane.

Workup

  1. customfitted
  2. temperaturewith cooling
  3. additionaddition period
  4. custom30 min
  5. stirringThe reaction mixture was then stirred at 35° for 17 hours
  6. temperatureafter cooling
  7. customAfter separation of the organic phase
  8. washwashing with 5% aqueous H2SO4 (200 ml)
  9. dry with materialdrying over Na2SO4, concentration
  10. distillationfinal distillation

Sources & evidence

ORD record
ord-d9fe5cac25264f2c9a620cc99ea05a47
Source dataset
uspto-grants-1982_06
Patent number
US04336197

Reaction notes

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