Acetic Acid → 1-phenylbut-3-yn-1-ol

HRID 259995Notes

Reaction equation

HRID 259995 reaction equation
Cl[C:2](=[CH2:12])[CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[OH-].[K+].C(O)(=O)C>CN(C)C=O>[C:6]1([CH:4]([CH2:3][C:2]#[CH:12])[OH:5])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 146636783-Chloro-1-phenyl-3-buten-1-ol

Product 1

HCID 110190061-phenylbut-3-yn-1-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40.00 Grams of 2-chloroallylphenylcarbinol were dissolved in 400 g of dimethylformamide, and 36.85 g of potassium hydroxide in a flake form were added. The mixture was stirred at room temperature for 2 hours and then neutralized with a 20% acetic acid aqueous solution. 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 the toluene was distilled off under reduced pressure to give 31.35 g of phenylpropargylcarbinol, nD20 =1.546, FI-MS m/e 146 (M+), propargyl compound/allene compound=92.3/7.7.

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

Sources & evidence

ORD record
ord-8c0ad265f0964247978ea5143783c4db
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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