4-Phenoxyphenyl propargyl ether → 6-phenoxy-2H-1-benzopyran

HRID 466189Notes

Reaction equation

HRID 466189 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[C:2]#[CH:3]>C(N(CC)C1C=CC=CC=1)C>[O:11]([C:8]1[CH:9]=[CH:10][C:5]2[O:4][CH2:1][CH:2]=[CH:3][C:6]=2[CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 99911924-Phenoxyphenyl propargyl ether

Product 1

HCID 198156156-phenoxy-2H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Conditions

Temperature
220 °C

Procedure

4-Phenoxyphenyl propargyl ether (33.7 g, 150 mmol) in 50 mL of N,N-diethylaniline is added to refluxing (220° C.) N,N-diethylanile (300 ml) dropwise over a period of 10 minutes under nitrogen. The mixture is stirred at reflux for 8 hours, cooled and evaporated under high vacuum (bath temp. ~80° C.) to remove solvents. The residue is distilled to give 6-phenoxy-2H-1-benzopyran; b.p. 147°-150° C./0.5 mmHg.

Workup

  1. temperatureat reflux for 8 hours
  2. temperaturecooled
  3. customevaporated under high vacuum (bath temp. ~80° C.)
  4. customto remove solvents
  5. distillationThe residue is distilled

Sources & evidence

ORD record
ord-748a7858fe184cc8bed263fd3a791c92
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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