Dimethylformamide → 1-(Benzyloxy)-2-{[(2,6-dichlorophenyl)methoxy]methyl}butan-2-ol

Reaction equation

[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:3]=1[CH2:4][O:5][CH2:6][C:7]([CH3:11])([OH:10])[CH2:8][OH:9].[H-].[Na+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:27]N(C)C=O>>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:3]=1[CH2:4][O:5][CH2:6][C:7]([CH2:11][CH3:27])([OH:10])[CH2:8][O:9][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 7503Benzyl Chloride

HCID 24758Sodium hydride

HCID 214964103-[(2,6-Dichlorophenyl)methoxy]-2-methylpropane-1,2-diol

Product 1

HCID 214964091-(Benzyloxy)-2-{[(2,6-dichlorophenyl)methoxy]methyl}butan-2-ol

Procedure

1-(2,6-Dichlorobenzyloxymethyl)-1-methylethane-1,2-diol (14g) in dimethyl formamide (80 ml) was treated with sodium hydride (1.3 g) at ambient temperature and stirred for 12 h. Benzyl chloride (8 g) was then added and the reaction mixture stirred for a further 4 h. The solvent was then evaporated and 1-(2,6-dichlorobenzyloxy)-3 -benzyloxy-2-ethylpropan-2-ol isolated as a colourless oil by chromatography on silica gel eluted with 9/1 methylene chloride/ether. The structure was confirmed by n.m.r. techniques.