Water → 1,1',1''-{[(Hex-5-yn-3-yl)oxy]methanetriyl}tribenzene

HRID 1395156Notes

Reaction equation

HRID 1395156 reaction equation
[OH:1][CH:2]([CH2:6][CH3:7])[CH2:3][C:4]#[CH:5].[C:8]1([C:14](Cl)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>N1C=CC=CC=1>[C:8]1([C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:1][CH:2]([CH2:6][CH3:7])[CH2:3][C:4]#[CH:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6456Trityl chlorideHCID 892235-Hexyn-3-ol

Product 1

HCID 205651061,1',1''-{[(Hex-5-yn-3-yl)oxy]methanetriyl}tribenzene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred solution of 9.81 g (0.10 moles) of 4-hydroxy-1-hexyne and 33.5 g (0.12 moles) of triphenylmethyl chloride in 100 ml of dry pyridine is heated at reflux for 2 hours. The cooled mixture is treated with water and extracted with a hexane-ether mixture. The extract is washed successively with water and saturated sodium chloride solution, dired over magnesium sulfate, and concentrated. Column chromatography of the residue on Florisil gives an oil, max. 3290 (acetylenic hydrogen), 1600, 1030 and 705 cm-1 (triphenylmethoxy group).

Workup

  1. temperatureat reflux for 2 hours
  2. extractionextracted with a hexane-ether mixture
  3. washThe extract is washed successively with water and saturated sodium chloride solution
  4. concentrationconcentrated
  5. customColumn chromatography of the residue on Florisil gives an oil, max

Sources & evidence

ORD record
ord-443e50eec2734b6fa6d3f70a206f2b8f
Source dataset
uspto-grants-1980_05
Patent number
US04202822

Reaction notes

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