Methyl Isobutyl Ketone → HCID 20344597, compound

HRID 2049854Notes

Reaction equation

HRID 2049854 reaction equation
[OH-:1].[K+].[CH3:3][C:4](=[CH2:7])[C:5]#[CH:6].[CH2:8]([C:12]([CH3:14])=O)[CH:9]([CH3:11])[CH3:10]>C1(C)C=CC=CC=1>[CH3:10][CH:9]([CH2:8][C:12]([CH3:14])([OH:1])[C:6]#[C:5][C:4]([CH3:7])=[CH2:3])[CH3:11]

Participants

5

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 14797Potassium HydroxideHCID 62323Isopropenylacetylene

Product 1

HCID 20344597HCID 20344597, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

400 ml of anhydrous toluene and 200 g of powdered potassium hydroxide are added to a 2 liter round flask which is provided with a stirrer, condenser, thermometer and dropping funnel. The mixture is cooled to -20° C. and there are now added thereto at a temperature between -20° C. and -10° C. 66g (1 mol) of 3-methyl-3-buten-1-yne [A. F. Thompson jun. N. A. Milas, Ida Rovno, J. Am. Chem. Soc. 63, (1941), 752-755]. The mixture is held at a temperature of -10° C. for 1.5 hours while stirring and there are slowly added thereto at 0° C. 110 g (1.1 mol) of methyl isobutyl ketone. The mixture is now stirred at 0° C. for 1 hour and then the temperature is allowed to rise to 20° C. within 2 hours with further stirring. The mixture is added to ice, extracted with 500 ml of toluene and washed with brine until neutral. The solvent is then evaporated. There are obtained 183 g of crude product, distillation of which yields 129.5 g (78.4%) of 2,4,7-trimethyl-7-octen-5-yn-4-ol of boiling point 76°-77° C./5 mmHg; nD20 =1.4690; d420 =0.8620.

Workup

  1. customis provided with a stirrer, condenser
  2. additionthere are now added
  3. customat a temperature between -20° C. and -10° C
  4. additionthere are slowly added
  5. customat 0° C
  6. stirringThe mixture is now stirred at 0° C. for 1 hour
  7. waitto rise to 20° C. within 2 hours with further stirring
  8. additionThe mixture is added to ice
  9. extractionextracted with 500 ml of toluene
  10. washwashed with brine until neutral
  11. customThe solvent is then evaporated
  12. customThere are obtained
  13. distillation183 g of crude product, distillation of which

Sources & evidence

ORD record
ord-6e614083551148129b9e490dff9dabb7
Source dataset
uspto-grants-1980_04
Patent number
US04198532

Reaction notes

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