Water → 1-Chloro-4-phenoxybut-2-yne

HRID 362261Notes

Reaction equation

HRID 362261 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O.[Cl:11][CH2:12][C:13]#[C:14][CH2:15]Cl>C(O)C>[Cl:11][CH2:12][C:13]#[C:14][CH2:15][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 131821,4-Dichloro-2-butyneHCID 14797Potassium Hydroxide

Product 1

HCID 109430691-Chloro-4-phenoxybut-2-yneYield 53.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
30 °C

Procedure

A mixture of phenol (50.8 g), potassium hydroxide (30 g), ethanol (200 ml) and water (50 ml) was stirred and heated under reflux for 1 hour, then cooled to 30° C. A solution of 1,4-dichlorobut-2-yne (100 g) in ethanol (60 ml) was added dropwise over 3.5 hours, then the mixture was stirred at ambient temperature for 18 hours and filtered. The filter cake was washed with ethanol (60 ml), and the filtrate and washings were combined. The solvents were removed in vacuo, and the residue was distilled to give 1-chloro-4-phenoxybut-2-yne as a colourless oil (52.5 g), b.p. 92°-98° C. at 0.53 mbar.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. stirringthe mixture was stirred at ambient temperature for 18 hours
  4. filtrationfiltered
  5. washThe filter cake was washed with ethanol (60 ml)
  6. customThe solvents were removed in vacuo
  7. distillationthe residue was distilled

Sources & evidence

ORD record
ord-b1c1d1d35a734fb2bbb5e2fac3e067d9
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Reaction notes

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