Benzyl Chloride → 1,3-Bis(benzyloxy)-2-methylpropan-2-ol

HRID 1730711Notes

Reaction equation

HRID 1730711 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.C(Cl)Cl.CCOCC>CN(C)C=O>[CH2:1]([O:8][CH2:9][C:10]([CH3:14])([OH:13])[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

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 561596HCID 561596, compoundHCID 21881112Ethyl ether methylene chloride

Product 1

HCID 214964031,3-Bis(benzyloxy)-2-methylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 -Benzyloxymethyl-1-methyl-ethane-1, 2-diol (5g) in dimethylformamide (25 ml) was treated with sodium hydride (0.65g), the reaction mixture was stirred at ambient temperature for 1 h. then at 90° C for 15 min. The reaction mixture was cooled and benzyl chloride (3.3g) added; it was stirred for 4 h. at ambient temperature. The solvent was evaporated and the product isolated by chromatography on silica gel using methylene chloride/ether (9/1) to give the desired product as a colourless oil. The 1,3-configuration was confirmed by n.m.r. which showed the methylene groups of the carbon backbone to be equivalent, hence, establishing the symmetry of the molecule.

Workup

  1. waitat 90° C for 15 min
  2. temperatureThe reaction mixture was cooled
  3. stirringit was stirred for 4 h. at ambient temperature
  4. customThe solvent was evaporated
  5. customthe product isolated by chromatography on silica gel

Sources & evidence

ORD record
ord-cb7ac4a9f103449fbd445f9c32b63eae
Source dataset
uspto-grants-1976_11
Patent number
US03993698

Reaction notes

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