Benzyl Chloride → 1,1',1''-[(2-Methylpropane-1,2,3-triyl)tris(oxymethylene)]tribenzene

HRID 1730712Notes

Reaction equation

HRID 1730712 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH3:14])([OH:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:1]([O:8][CH2:9][C:10]([O:13][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:14])[CH2:11][O:12][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 561596HCID 561596, compound

Product 1

HCID 214964061,1',1''-[(2-Methylpropane-1,2,3-triyl)tris(oxymethylene)]tribenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 Benzyloxymethyl-1-methylethane-1,2-diol (2g) in dimethyl formamide (25 ml) was treated with a slight excess of sodium hydride (0.6g) at ambient temperature for 1h, then 90° for 15 mins. The product was then treated with benzyl chloride (4g) and 1,2,3-tribenzyloxy-2-methylpropane was isolated by evaporation of the solvent followed by chromatography on silica gel eluted with 9/1 methylene chloride/ether. The desired product was a colourless oil whose structure was confirmed by n.m.r.

Sources & evidence

ORD record
ord-f020917c87fc41d39105f9f736dec117
Source dataset
uspto-grants-1976_11
Patent number
US03993698

Reaction notes

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