Acetic Acid → HCID 57195083, compound

HRID 256731Notes

Reaction equation

HRID 256731 reaction equation
Cl[C:2]([CH2:4][C:5]([CH3:11])([OH:10])[CH:6]=[C:7]([CH3:9])[CH3:8])=[CH2:3].[OH-].[K+].C(O)(=O)C>CN(C)C=O>[CH3:11][C:5]([CH2:6][C:7]([CH3:9])=[CH2:8])([CH2:4][C:2]#[CH:3])[OH:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 22404526HCID 22404526, compound

Product 1

HCID 57195083HCID 57195083, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.00 Grams of the 2-chloro-4,6-dimethyl-1,5-heptadien-4-ol obtained above were dissolved in 94 g of N,N-dimethylformamide, and 9.65 g of potassium hydroxide in a flake form were added. The resultant mixture was stirred at room temperature for 4 hours and neutralized with a 20% acetic acid aqueous solution, and the resultant mixture was subjected to extraction with toluene. The toluene phase was washed with water and then dried over magnesium sulfate. The desiccant was filtered off, and then the toluene was distilled off under reduced pressure. The resultant oily substance was purified by silica gel column chromatography to give 6.32 g of methyl 2-methylallylpropargylcarbinol; nD25 =1.496, FI-MS m/e 138 (M+) (Propargyl compound/allene compound=100.0/0.0).

Workup

  1. extractionthe resultant mixture was subjected to extraction with toluene
  2. washThe toluene phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. distillationthe toluene was distilled off under reduced pressure
  6. customThe resultant oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd83d773ca16424eaac1830cc58b3a27
Source dataset
uspto-grants-1993_11
Patent number
US05258529

Reaction notes

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