Dimethylformamide → [(2,3-Dimethoxy-2-methylpropoxy)methyl]benzene

HRID 1730714Notes

Reaction equation

HRID 1730714 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH3:14])(O)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:17]I.CN(C)[CH:21]=[O:22]>>[CH3:17][O:12][CH2:11][C:10]([O:22][CH3:21])([CH3:14])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 561596HCID 561596, compound

Product 1

HCID 21496407[(2,3-Dimethoxy-2-methylpropoxy)methyl]benzene

Procedure

1-(Benzyloxymethyl)-1-methylethane-1,2-diol (10 g) and sodium hydride (1.2 g) were stirred together in dimethyl formamide (50 ml) for 12 h; the reaction mixture was then treated with methyl iodide (7.1g) and again stirred for 4 h. The reaction product was then stripped at 100°/1 mm and the residue purified by chromatography on silica gel eluted with 9/1 methylene chloride/ether to give a small forerun of 1,2-dimethoxy-2-methyl-3-benzyloxypropane and then 11 g 1-methoxy-3-benzyloxy-2-methylpropan-2-ol as a colourless oil. The structure was confirmed by n.m.r. techniques.

Workup

  1. customwas then stripped at 100°
  2. customthe residue purified by chromatography on silica gel
  3. washeluted with 9/1 methylene chloride/ether

Sources & evidence

ORD record
ord-1a81ab8cc75a4b2dbf0b9d5b38a8394a
Source dataset
uspto-grants-1976_11
Patent number
US03993698

Reaction notes

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