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

HRID 127053Notes

Reaction equation

HRID 127053 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, dried 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. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customColumn chromatography of the residue on Florisil gives an oil, max

Sources & evidence

ORD record
ord-cf4f0c31f49e4640a2294844a8c01928
Source dataset
uspto-grants-1981_03
Patent number
US04254285

Reaction notes

Loading…